CH589063A5 - 3,4-Dihydro-1(2H)-phthalazinones prepn - by hydrogenating and hydrolysing 2-acyl-3,4-unsaturated cpds. - Google Patents

3,4-Dihydro-1(2H)-phthalazinones prepn - by hydrogenating and hydrolysing 2-acyl-3,4-unsaturated cpds.

Info

Publication number: CH589063A5
Authority: CH; Switzerland
Prior art keywords: dihydro; formula; phthalazinone; hydrogenation; acyl
Prior art date: 1973-04-27

Application number

CH569374A

Other languages

English (en)

French (fr)

Original Assignee

Lepetit Spa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-04-27

Filing date

1974-04-25

Publication date

1977-06-30

1974-04-25 Application filed by Lepetit Spa filed Critical Lepetit Spa

1977-06-30 Publication of CH589063A5 publication Critical patent/CH589063A5/fr

Links

KCOLJRSQFLZEAB-UHFFFAOYSA-N 3,4-dihydro-2h-phthalazin-1-one Chemical class C1=CC=C2C(=O)NNCC2=C1 KCOLJRSQFLZEAB-UHFFFAOYSA-N 0.000 title claims abstract description 9
230000003301 hydrolyzing effect Effects 0.000 title abstract 2
239000002253 acid Substances 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 9
239000003054 catalyst Substances 0.000 claims abstract description 6
239000002904 solvent Substances 0.000 claims abstract description 6
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 5
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims abstract description 4
-1 and R1 is H Chemical group 0.000 claims abstract description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
229910052763 palladium Inorganic materials 0.000 claims abstract description 4
229910052697 platinum Inorganic materials 0.000 claims abstract description 4
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims abstract description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract description 3
125000002252 acyl group Chemical group 0.000 claims abstract description 3
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 3
239000011707 mineral Substances 0.000 claims abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
229910019020 PtO2 Inorganic materials 0.000 claims abstract 3
238000000034 method Methods 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
239000007868 Raney catalyst Substances 0.000 claims description 4
229910000564 Raney nickel Inorganic materials 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 3
229910052703 rhodium Inorganic materials 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 2
150000007513 acids Chemical class 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
229910052702 rhenium Inorganic materials 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical group C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 9
DSKMUWSWZNCOLF-UHFFFAOYSA-N 3,4-dihydro-2H-phthalazin-1-one hydrochloride Chemical compound Cl.O=C1NNCc2ccccc12 DSKMUWSWZNCOLF-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000007858 starting material Substances 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
ZLHNYIHIHQEHJQ-UHFFFAOYSA-N N,N'-Diacetylhydrazine Chemical compound CC(=O)NNC(C)=O ZLHNYIHIHQEHJQ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
NKWOXRUJRCMCBH-UHFFFAOYSA-N 1,3-dihydroisoindol-2-amine Chemical class C1=CC=C2CN(N)CC2=C1 NKWOXRUJRCMCBH-UHFFFAOYSA-N 0.000 description 1
FACXGJANFZCRTJ-UHFFFAOYSA-N 2,3-diacetyl-4H-phthalazin-1-one Chemical compound C(C)(=O)N1C(C2=CC=CC=C2CN1C(C)=O)=O FACXGJANFZCRTJ-UHFFFAOYSA-N 0.000 description 1
ZSCSUJZQCNTODA-UHFFFAOYSA-N 2-(bromomethyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1CBr ZSCSUJZQCNTODA-UHFFFAOYSA-N 0.000 description 1
PZTWFIMBPRYBOD-UHFFFAOYSA-N 2-acetylphthalazin-1-one Chemical compound C1=CC=C2C(=O)N(C(=O)C)N=CC2=C1 PZTWFIMBPRYBOD-UHFFFAOYSA-N 0.000 description 1
UKUHYPJXWWZLMR-UHFFFAOYSA-N 2-benzoyl-3,4-dihydrophthalazin-1-one Chemical compound C(C1=CC=CC=C1)(=O)N1C(C2=CC=CC=C2CN1)=O UKUHYPJXWWZLMR-UHFFFAOYSA-N 0.000 description 1
QCKGMJDOJRNSMS-UHFFFAOYSA-N 4-chloro-2h-phthalazin-1-one Chemical compound C1=CC=C2C(Cl)=NNC(=O)C2=C1 QCKGMJDOJRNSMS-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Furan Compounds (AREA)

CH569374A 1973-04-27 1974-04-25 3,4-Dihydro-1(2H)-phthalazinones prepn - by hydrogenating and hydrolysing 2-acyl-3,4-unsaturated cpds. CH589063A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2019973		1973-04-27

Publications (1)

Publication Number	Publication Date
CH589063A5 true CH589063A5 (en)	1977-06-30

Family

ID=10142061

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH569374A CH589063A5 (en)	1973-04-27	1974-04-25	3,4-Dihydro-1(2H)-phthalazinones prepn - by hydrogenating and hydrolysing 2-acyl-3,4-unsaturated cpds.

Country Status (7)

Country	Link
JP (1)	JPS5013381A (cs)
CH (1)	CH589063A5 (cs)
CS (1)	CS178915B2 (cs)
DD (1)	DD110870A5 (cs)
HU (1)	HU168063B (cs)
PL (1)	PL96487B1 (cs)
SU (1)	SU539526A3 (cs)

1974
- 1974-04-25 CH CH569374A patent/CH589063A5/fr not_active IP Right Cessation
- 1974-04-25 PL PL17058274A patent/PL96487B1/pl unknown
- 1974-04-26 DD DD17816374A patent/DD110870A5/xx unknown
- 1974-04-26 JP JP4745174A patent/JPS5013381A/ja active Pending
- 1974-04-26 SU SU2019281A patent/SU539526A3/ru active
- 1974-04-26 HU HULE000744 patent/HU168063B/hu unknown
- 1974-04-26 CS CS300974A patent/CS178915B2/cs unknown

Also Published As

Publication number	Publication date
CS178915B2 (en)	1977-10-31
JPS5013381A (cs)	1975-02-12
PL96487B1 (pl)	1977-12-31
SU539526A3 (ru)	1976-12-15
DD110870A5 (cs)	1975-01-12
HU168063B (cs)	1976-02-28

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Legal Events

Date	Code	Title	Description
1980-02-15	PL	Patent ceased
2024-10-31	PL	Patent ceased