IES86950B2 - Drug intermediates o-aminobenzaldehyde synthesis method - Google Patents
Drug intermediates o-aminobenzaldehyde synthesis methodInfo
- Publication number
- IES86950B2 IES86950B2 IES20180094A IES20180094A IES86950B2 IE S86950 B2 IES86950 B2 IE S86950B2 IE S20180094 A IES20180094 A IE S20180094A IE S20180094 A IES20180094 A IE S20180094A IE S86950 B2 IES86950 B2 IE S86950B2
- Authority
- IE
- Ireland
- Prior art keywords
- solution
- mol
- aminobenzaldehyde
- mass fraction
- synthesis method
- Prior art date
Links
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000000543 intermediate Substances 0.000 title claims abstract description 10
- 239000003814 drug Substances 0.000 title claims abstract description 8
- 229940079593 drug Drugs 0.000 title claims abstract description 8
- 238000001308 synthesis method Methods 0.000 title claims abstract description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 14
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 8
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims abstract description 6
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims abstract description 6
- 239000013078 crystal Substances 0.000 claims abstract description 6
- 229940045803 cuprous chloride Drugs 0.000 claims abstract description 6
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000005292 vacuum distillation Methods 0.000 claims abstract description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 229940095564 anhydrous calcium sulfate Drugs 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 1
- 229940095672 calcium sulfate Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Drug intermediates o-aminobenzaldehyde synthesis method, comprises the following steps: the reaction vessel was added 2 mol o-nitrobenzaldehyde, 50 L water, 3-4 mol cuprous chloride, 5-6 mol 2-aminotoluene, the stirring rate was controlled at 90-130 rpm, and the temperature of the solution was raised to 70-75°C, reaction for 70-90min, vacuum distillation, collecting fraction of 80-86°C, collecting distillate, add 1-2kg potassium bromide, reduce the solution temperature to 5-8°C, after the crystal precipitated, filter it, washed with the dimethylmine solution and with trifluoroacetic acid solution, dehydrating with the dehydrating agent and recrystallized in the ethane solution to obtain the finished product.
Description
The present invention relates to drug intermediates o-aminobenzaldehyde synthesis method.
GENERAL BACKGROUND
O-aminobenzaldehyde is mainly used for organic synthesis intermediates, dyes raw materials, pharmaceutical raw materials. However, most of the existing synthetic methods are complicated and the final yield is not very high. Therefore, it is necessary to propose a new synthetic method for further improving the quality and yield of the product and reducing the byproduct content, it has important economic significance.
SUMMARY
The purpose of the present invention is to provide drug intermediates o-aminobenzaldehyde synthesis method, comprises the following steps:
(i) the reaction vessel was added 2 mol o-nitrobenzaldehyde, 50 L water, 3-4 mol cuprous chloride, 5-6 mol 2-aminotoluene, the stirring rate was controlled at 90-130 rpm, and the temperature of the solution was raised to 70-75 °C, reaction for 70-90min, vacuum distillation, collecting fraction of 80-86°C, collecting distillate, add 1-2kg potassium bromide, reduce the solution temperature to 5-8 °C, after the crystal precipitated, filter it, washed with the dimethylmine solution and with trifluoroacetic acid solution, dehydrating with the dehydrating agent and recrystallized in the ethane solution to obtain the finished product; wherein the mass fraction of the dimethylamine solution in the step (i) has a mass fraction of 70-76%, the trifluoroacetic acid solution in the step (i) has a mass fraction of 80-85%, and the dehydrating agent in the step (i) is any one of anhydrous calcium sulfate and anhydrous potassium carbonate, and the ethane solution in step (i) has a mass fraction of 90-93%.
Advantage of the present invention is that: reducing intermediate links reaction, decreasing the reaction time and improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invention are further illustrated:
drug intermediates o-aminobenzaldehyde synthesis method.
Embodiment 1 mol o-nitrobenzaldehyde, 50 L water, 3 mol cuprous chloride and 5 mol 2-aminotoluene were added to the reaction vessel, the stirring speed was controlled to 90 rpm and the temperature of the solution was increased to 70 °C, reacted for 70 min, fractions of 80 °C were collected and the distillate was collected, and 1 kg potassium bromide was added., the temperature of the solution was reduced to 50 °C, and the crystals were separated and filtered, washed with dimethylamine solution with a mass fraction of 70%, and with trifluoroacetic acid solution with a mass fraction of 80%, dehydrated with calcium sulfate dehydrating agent, recrystallized in 90% ethane solution to obtain the finished product o-amino.benzaldehyde 215.38 g, yield 89%.
Embodiment 2 mol o-nitrobenzaldehyde, 50 L water, 3.5 mol cuprous chloride and 5.5 mol 2-aminotoluene were added to the reaction vessel, the stirring speed was controlled at 110 rpm, the solution temperature was increased to 72 °C, fractions of 83 ° C were collected and the distillate was collected, 1.5 kg potassium bromide was added and the temperature o f the solution was reduced to 6 ° C, the crystals were separated, filtered, washed with dimethylamine solution with a mass fraction of 73%, and with trifluoroacetic acid solution with a mass fraction of 83%, dehydrated with anhydrous potassium carbonate dehydrating agent, recrystallized in the ethane solution with a mass fraction of 91% to obtain the finished product o-amino benzaldehyde 222.64g, yield 92%.
Embodiment 3
2mol o-nitrobenzaldehyde, 50L water, 4mol cuprous chloride and 6mol 2-aminotoluene were added to the reaction vessel, the stirring speed was controlled at 130rpm, the temperature the solution was increased to 75°C, fractions of 86 ° C were collected and the distillate was collected, adding 2kg potassium bromide, reducing the solution temperature to 80 °C, the crystals precipitated, filtering, washed with dimethylamine solution with a mass fraction of 76%, and with trifluoroacetic acid solution with a mass fraction of 85%, dehydrated with anhydrous calcium sulfate dehydrating agent, recrystallized in the mass fraction of 93% ethane solution, to obtain the finished product o-amino benzaldehyde 229.9g, the yield of 95%.
Claims
Claims (3)
1. I. Drug intermediates o-aminobenzaldehyde synthesis method, comprises the following steps: (i) the reaction vessel was added
2. Mol o-nitrobenzaldehyde, 50 L water, 3-4 mol 5 cuprous chloride, 5-6 mol 2-aminotoluene, the stirring rate was controlled at 90-130 rpm, and the temperature of the solution was raised to 70-75 °C, reaction for 70-90min, vacuum distillation, collecting fraction of 80-86°C, collecting distillate, add I-2kg potassium bromide, reduce the solution temperature to 5-8°C, after the crystal precipitated, filter it, washed with the dimethylmine solution and with trifluoroacetic 10 acid solution, dehydrating with the dehydrating agent and recrystallized in the ethane solution to obtain the finished product; wherein the mass fraction of the dimethylamine solution in the step (i) has a mass fraction of 70-76%. the trifluoroacetic acid solution in the step (i) has a mass fraction of 80-85%. 15 2. Drug intermediates o-aminobenzaldehyde synthesis method according to claim 1 wherein the dehydrating agent in the step (i) is any one of anhydrous calcium sulfate and anhydrous potassium carbonate.
3. Drug intermediates o-aminobenzaldehyde synthesis method according to claim 20 1 wherein the ethane solution in step (i) has a mass fraction of 90-93%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IES20180094A IES20180094A2 (en) | 2018-04-03 | 2018-04-03 | Drug intermediates o-aminobenzaldehyde synthesis method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IES20180094A IES20180094A2 (en) | 2018-04-03 | 2018-04-03 | Drug intermediates o-aminobenzaldehyde synthesis method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IES86950B2 true IES86950B2 (en) | 2019-01-09 |
| IES20180094A2 IES20180094A2 (en) | 2019-01-09 |
Family
ID=65009472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IES20180094A IES20180094A2 (en) | 2018-04-03 | 2018-04-03 | Drug intermediates o-aminobenzaldehyde synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| IE (1) | IES20180094A2 (en) |
-
2018
- 2018-04-03 IE IES20180094A patent/IES20180094A2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IES20180094A2 (en) | 2019-01-09 |
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