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

HRID 1384504Notes

Reaction equation

HRID 1384504 reaction equation
O.O[PH2]=O.[P].[CH2:6]([O:9][C:10](=[O:27])[C:11]([O:14][C:15](=[O:26])[C:16]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:17]=1[Cl:25])([CH3:13])[CH3:12])[CH:7]=[CH2:8]>[Pt].C1(C)C=CC=CC=1>[CH2:6]([O:9][C:10](=[O:27])[C:11]([O:14][C:15](=[O:26])[C:16]1[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][C:17]=1[Cl:25])([CH3:13])[CH3:12])[CH:7]=[CH2:8]

Participants

7

Reactant 4

HCID 962WaterHCID 4124402Phosphinic AcidHCID 5462309PhosphorusHCID 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 98.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

5.9 kg of 5% Pt/C catalyst 5% (H2O content: 62.8%) are placed in a 60-liter steel vessel together with 12 liters of water, and 470 g of 50% H3PO2 solution (≡5% phosphorus based on the catalyst) are added. The catalyst slurry is stirred for 10 minutes at room temperature, then 360 g of vanadylacetylacetonate VO(acac)2 as is (0.2 mol %) are added and the mixture is stirred for a further 5 minutes. 550 kg of a solution of 2-(chloro-5-nitro-benzoyl-oxy)-2-methyl-propionic acid allyl ester (content: 40%, 0.67 kmol) in toluene are placed in an autoclave having a stirrer and the catalyst suspension is added, rinsing the steel vessel with 15 kg of water. Hydrogenation is then carried out for 2 hours at a temperature of 100° C. and a hydrogen pressure of 5 bar. After cooling and rendering the autoclave inert using nitrogen, the catalyst is filtered off at 50° C. and washed with 50 kg of toluene. After working up by distillation, 196 kg of 2-(chloro-5-amino-benzoyloxy)-2-methyl-propionic acid allyl ester (yield 98% of theory) are obtained. The over-hydrogenated propyl ester content is <0.05%.

Workup

  1. additionare added
  2. additionare added
  3. stirringthe mixture is stirred for a further 5 minutes
  4. additionthe catalyst suspension is added
  5. washrinsing the steel vessel with 15 kg of water
  6. waitHydrogenation is then carried out for 2 hours at a temperature of 100° C.
  7. temperatureAfter cooling
  8. filtrationthe catalyst is filtered off at 50° C.
  9. washwashed with 50 kg of toluene

Sources & evidence

ORD record
ord-30acfdfcd19f4fe39033e26cc8e7529b
Source dataset
uspto-grants-2001_07
Patent number
US06258982B1

Reaction notes

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