CH403790A - Verfahren zur Darstellung von o,o'-disubstituierten m-Aminobenzoesäurederivaten - Google Patents

Verfahren zur Darstellung von o,o'-disubstituierten m-Aminobenzoesäurederivaten

Info

Publication number: CH403790A
Authority: CH; Switzerland
Prior art keywords: disubstituted; nitro; preparation; formula; reacting
Prior art date: 1960-01-21

Application number

CH71461A

Other languages

German (de)

English (en)

Inventor

Jaakko Juhani Dr Techn Hukki

Juhani Honkanen Erkki

Original Assignee

Laaketehdas Orion Oy

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.)

1960-01-21

Filing date

1961-01-20

Publication date

1965-12-15

1961-01-20 Application filed by Laaketehdas Orion Oy filed Critical Laaketehdas Orion Oy

1965-12-15 Publication of CH403790A publication Critical patent/CH403790A/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 5
238000000034 method Methods 0.000 title claims description 7
XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical class NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 title description 4
-1 ortho-disubstituted m-nitrobenzoic acid halide Chemical class 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
150000002828 nitro derivatives Chemical class 0.000 claims description 6
239000007868 Raney catalyst Substances 0.000 claims description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
229910000564 Raney nickel Inorganic materials 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
GSCPDZHWVNUUFI-UHFFFAOYSA-N 3-aminobenzamide Chemical class NC(=O)C1=CC=CC(N)=C1 GSCPDZHWVNUUFI-UHFFFAOYSA-N 0.000 claims description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000001302 tertiary amino group Chemical group 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 5
125000004663 dialkyl amino group Chemical group 0.000 abstract 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
KLGQWSOYKYFBTR-UHFFFAOYSA-N 2-nitrobenzamide Chemical compound NC(=O)C1=CC=CC=C1[N+]([O-])=O KLGQWSOYKYFBTR-UHFFFAOYSA-N 0.000 abstract 1
XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 abstract 1
150000001408 amides Chemical class 0.000 abstract 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
125000004430 oxygen atom Chemical group O* 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000005984 hydrogenation reaction Methods 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000009835 boiling Methods 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000003589 local anesthetic agent Substances 0.000 description 2
ALFLTCILZQYZQW-UHFFFAOYSA-N 2,6-dimethyl-3-nitrobenzoyl chloride Chemical compound CC1=CC=C([N+]([O-])=O)C(C)=C1C(Cl)=O ALFLTCILZQYZQW-UHFFFAOYSA-N 0.000 description 1
HKUYLJOKQXCBDY-UHFFFAOYSA-N 2-(2-methylpropylamino)ethyl 3-aminobenzoate;hydrochloride Chemical compound Cl.CC(C)CNCCOC(=O)C1=CC=CC(N)=C1 HKUYLJOKQXCBDY-UHFFFAOYSA-N 0.000 description 1
PZDZCIBGBFLKNO-UHFFFAOYSA-N C(C)C1=C(C(=O)Cl)C(=CC=C1[N+](=O)[O-])CC Chemical compound C(C)C1=C(C(=O)Cl)C(=CC=C1[N+](=O)[O-])CC PZDZCIBGBFLKNO-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH71461A 1960-01-21 1961-01-20 Verfahren zur Darstellung von o,o'-disubstituierten m-Aminobenzoesäurederivaten CH403790A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FI9260		1960-01-21

Publications (1)

Publication Number	Publication Date
CH403790A true CH403790A (de)	1965-12-15

Family

ID=8503586

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH71461A CH403790A (de)	1960-01-21	1961-01-20	Verfahren zur Darstellung von o,o'-disubstituierten m-Aminobenzoesäurederivaten

Country Status (4)

Country	Link
BE (1)	BE599215A (fr)
CH (1)	CH403790A (fr)
DE (1)	DE1247323B (fr)
GB (1)	GB910257A (fr)

1961
- 1961-01-18 BE BE599215A patent/BE599215A/fr unknown
- 1961-01-18 DE DEL37973A patent/DE1247323B/de active Pending
- 1961-01-20 GB GB232661A patent/GB910257A/en not_active Expired
- 1961-01-20 CH CH71461A patent/CH403790A/de unknown

Also Published As

Publication number	Publication date
DE1247323B (de)	1967-08-17
GB910257A (en)	1962-11-14
BE599215A (fr)	1961-05-16

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