Toluene → 5-Amino-2-chlorobenzoic acid 1-allyloxycarbonyl-1-methyl-ethyl ester

HRID 1384503Notes

Reaction equation

HRID 1384503 reaction equation
[CH2:1]([O:4][C:5](=[O:22])[C:6]([O:9][C:10](=[O:21])[C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=1[Cl:20])([CH3:8])[CH3:7])[CH:2]=[CH2:3].C1(C)C=CC=CC=1.[PH2](O)=O>[Pt].[C].[V].O>[CH2:1]([O:4][C:5](=[O:22])[C:6]([O:9][C:10](=[O:21])[C:11]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:12]=1[Cl:20])([CH3:8])[CH3:7])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 1140TolueneHCID 4124402Phosphinic AcidHCID 117823921-(Allyloxy)-2-methyl-1-oxopropan-2-yl 2-chloro-5-nitrobenzoate

Product 1

HCID 109685095-Amino-2-chlorobenzoic acid 1-allyloxycarbonyl-1-methyl-ethyl esterYield 94.8%

Reagents, catalysts & solvents 3

HCID 23990VanadiumCatalystHCID 178503042HCID 178503042, compoundCatalystHCID 962WaterSolvent

Procedure

0.9 g of vanadium-containing active carbon prepared according to Example A1 is added to a solution of 16.1 g of 2-(2-chloro-5-nitrobenzoyloxy)-2-methyl-propionic acid allyl ester and 100 mg of toluene in an autoclave having a stirrer. 82 mg of platinum-carbon catalyst together with 50 mg of hypophosphorous acid and 2 ml of deionised water are placed in a seperate glass vessel, and the mixture is stirred for 10 minutes. The catalyst suspension is then transferred to the autoclave, rinsing the glass vessel with 4 ml of deionised water, and hydrogenated for 2 hours at a temperature of 100° C. and a hydrogen pressure of 20 bar. After cooling and rendering the autoclave inert using nitrogen, the catalyst is filtered off and washed with 20 ml of toluene. After working up by distillation, 14 g of 2-(2-chloro-5-amino-benzoyloxy)-2-methyl-propionic acid allyl ester having a content of 98.9% according to HPLC are obtained (yield 94.8% of theory).

Workup

  1. customprepared
  2. washrinsing the glass vessel with 4 ml of deionised water
  3. waithydrogenated for 2 hours at a temperature of 100° C.
  4. temperatureAfter cooling
  5. filtrationthe catalyst is filtered off
  6. washwashed with 20 ml of toluene
  7. distillationAfter working up by distillation, 14 g of 2-(2-chloro-5-amino-benzoyloxy)-2-methyl-propionic acid allyl ester having a content of 98.9%
  8. customare obtained (yield 94.8% of theory)

Sources & evidence

ORD record
ord-a620dc1bde02438cb54e14cc86429f31
Source dataset
uspto-grants-2001_07
Patent number
US06258982B1

Reaction notes

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