1-(Allyloxy)-2-methyl-1-oxopropan-2-yl 2-chloro-5-nitrobenzoate → 5-Amino-2-chlorobenzoic acid 1-allyloxycarbonyl-1-methyl-ethyl ester

HRID 342241Notes

Reaction equation

HRID 342241 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:3]=1[C:4]([O:6][C:7]([CH3:15])([CH3:14])[C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])=[O:5].[H][H]>C(C(C)=O)C.[Cl-].C[N+](C)(C)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:3]=1[C:4]([O:6][C:7]([CH3:15])([CH3:14])[C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])=[O:5]

Participants

5

Reactant 2

HCID 117823921-(Allyloxy)-2-methyl-1-oxopropan-2-yl 2-chloro-5-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 109685095-Amino-2-chlorobenzoic acid 1-allyloxycarbonyl-1-methyl-ethyl esterYield 96.8%

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a stirred autoclave, 0.33 g of a catalyst prepared according to Example H1 is added to a solution of 65.5 g of allyl 2-(2-chloro-5-nitrobenzoyloxy)-2-methylpropionate in 370 g of methyl ethyl ketone, 0.2 g (0.5 mol %) of FeCl2 4H2O and 22 mg (0.1 mol %) of tetramethylammonium chloride are added in addition, and the mixture is hydrogenated for 5 hours at a temperature of 140° C. and at a hydrogen pressure of 15 bar. After cooling and flushing the stirred autoclave with nitrogen, the catalyst is filtered off and rinsed with 40 g of methyl ethyl ketone. 435.5 g are obtained of a solution having a content of 13.22% of allyl 2-(2-chloro-5-aminobenzoyloxy)-2-methylpropionate (yield: 96.8 % of theory).

Workup

  1. additionare added in addition
  2. temperatureAfter cooling
  3. customflushing the stirred autoclave with nitrogen
  4. filtrationthe catalyst is filtered off
  5. washrinsed with 40 g of methyl ethyl ketone
  6. custom435.5 g are obtained of a solution

Sources & evidence

ORD record
ord-06bc6bfbc348432182bf7365f30b09d3
Source dataset
uspto-grants-1999_01
Patent number
US05856578

Reaction notes

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