Prop-2-en-1-yl 3-nitrobenzoate → Allyl 3-aminobenzoate

HRID 2072334Notes

Reaction equation

HRID 2072334 reaction equation
[CH2:1]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)[CH:2]=[CH2:3]>CO.[Co]=S>[CH2:1]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 1

HCID 14980143Prop-2-en-1-yl 3-nitrobenzoate

Product 1

HCID 18930599Allyl 3-aminobenzoateYield 89.5%

Reagents, catalysts & solvents 2

HCID 14832Cobalt sulfideCatalystHCID 887MethanolSolvent

Procedure

478 g of 3-nitrobenzoic acid allyl ester are hydrogenated in 2 l of methanol at 110° C and 30-50 bars of H2 in the presence of 60 g of a cobalt sulphide paste which contains 30% of CoS3. The absorption of H2 has ceased in 2 hours. After cooling, 30 g of NaHCO3 are added to the methanol solution which contains the suspended catalyst and the mixture is stirred for 10 minutes and filtered. Distillation gives 366 g of 3-aminobenzoic acid allyl ester, boiling point 0.35 = 135° C; ND20 = 1.5657.

Workup

  1. customThe absorption of H2
  2. temperatureAfter cooling
  3. addition30 g of NaHCO3 are added to the methanol solution which
  4. filtrationfiltered
  5. distillationDistillation

Sources & evidence

ORD record
ord-da97bd8c040e4620a87a73af3fc81776
Source dataset
uspto-grants-1977_09
Patent number
US04051177

Reaction notes

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