Potassium Hydroxide → Methyl 3-amino-3-(3-nitrophenyl)prop-2-enoate

HRID 1762145

Reaction equation

HRID 1762145 reaction equation
[NH2:1][C:2](=[C:12](C(OC)=O)[C:13]([O:15][CH3:16])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[OH-].[K+]>CO.O>[NH2:1][C:2]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1)=[CH:12][C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 9970879Dimethyl (alpha-amino-3-nitrobenzylidene)malonate

Product 1

HCID 69855994Methyl 3-amino-3-(3-nitrophenyl)prop-2-enoateYield 52.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of dimethyl (α-amino-3-nitrobenzylidene)malonate (120 g) and potassium hydroxide in a mixture of methanol (1.2 l) and water (120 ml) was refluxed for 8 hours. The reaction mixture was concentrated under reduced pressure to a volume of 200 ml. The resulting crystals were collected by filtration and recrystallized from methanol to give methyl 3-amino-3-(3-nitrophenyl)acrylate (50.2 g).

Workup

  1. temperaturewas refluxed for 8 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure to a volume of 200 ml
  3. filtrationThe resulting crystals were collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-210b451c462e4d8c91a9756d124aec4e
Source dataset
uspto-grants-1989_05
Patent number
US04831030

Linked notes

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