Methyl 4-nitro-2-vinylbenzoate → Methyl 4-amino-2-ethylbenzoate

HRID 514275Notes

Reaction equation

HRID 514275 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH:14]=[CH2:15])[CH:5]=1)([O-])=O>CO>[NH2:1][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH2:14][CH3:15])[CH:5]=1

Participants

3

Reactant 1

HCID 57663378Methyl 4-nitro-2-vinylbenzoate

Product 1

HCID 57663468Methyl 4-amino-2-ethylbenzoateYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15.0 g (72.3 mmol) of methyl 4-nitro-2-vinylbenzoate in 150 ml of methanol were hydrogenated in an autoclave at 5 bar for 15 hours. The solution was filtered through kieselguhr, the solvent was distilled off under reduced pressure, and the residue was chromatographed using silica gel with cyclohexane/ethyl acetate (ratio 3:1) as the eluent. 2.4 g (24% of theory) of methyl 4-amino-2-ethylbenzoate were obtained.

Workup

  1. filtrationThe solution was filtered through kieselguhr
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue was chromatographed

Sources & evidence

ORD record
ord-346b583ea7ae43758d4b7420a4d12c97
Source dataset
uspto-grants-2015_08
Patent number
US09107411B2

Reaction notes

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