Ethyl 2-acetoxy-5-benzylideneaminobenzoate → Ethyl 2-acetoxy-5-aminobenzoate

HRID 2107016Notes

Reaction equation

HRID 2107016 reaction equation
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:13]([N:16]=CC2C=CC=CC=2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[CH3:2]>O.C(O)C>[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 23047223Ethyl 2-acetoxy-5-benzylideneaminobenzoate

Product 1

HCID 23047226Ethyl 2-acetoxy-5-aminobenzoateYield 42%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Ethyl 2-acetoxy-5-benzylideneaminobenzoate (10.0 g, 32.2 mmole) was refluxed in water-ethanol (3:1, 750 ml) for about 1 hour, after which time the mixture was cooled and the precipitate isolated by filtration. After a further recrystallization this gave the title compound (3.0 g, 42%), m.p. 82.5°-83° C. Found (Calc. for C11H13NO4) C 58.96 (59.19). H 5.98 (5.83), N 6.22 (6.28).

Workup

  1. temperatureafter which time the mixture was cooled
  2. customthe precipitate isolated by filtration
  3. customAfter a further recrystallization

Sources & evidence

ORD record
ord-c69dbda3f6724b44b4af56b86265de17
Source dataset
uspto-grants-1990_06
Patent number
US04933330

Reaction notes

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