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

HRID 342239Notes

Reaction equation

HRID 342239 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]>O1CCCC1.C(O)CC>[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 92.7%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a stirred autoclave, 0.1 g of a catalyst prepared according to Example H1 is added to a solution of 10 g of allyl 2-(2-chloro-5-nitrobenzoyloxy)-2-methylpropionate in 80 ml of tetrahydrofuran and 20 ml of n-propanol, and the mixture is hydrogenated for 15 hours at a temperature of 140° C. and at a hydrogen pressure of 20 bar. After cooling the mixture to room temperature and flushing the stirred autoclave with nitrogen, the catalyst is filtered off. 126.8 g (incl. rinsing solvent) are obtained of a solution having a content of 6.58% of allyl 2-(2-chloro-5-aminobenzoyloxy)-2-methylpropionate (yield: 92.7% of theory).

Workup

  1. customflushing the stirred autoclave with nitrogen
  2. filtrationthe catalyst is filtered off
  3. custom126.8 g (incl. rinsing solvent) are obtained of a solution

Sources & evidence

ORD record
ord-51f70b11c5754dcdb78d7a20deeded8a
Source dataset
uspto-grants-1999_01
Patent number
US05856578

Reaction notes

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