Benzaldehyde → Methyl 2-hydroxy-5-benzylideneaminobenzoate

HRID 2107009Notes

Reaction equation

HRID 2107009 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 135127Methyl 5-amino-2-hydroxybenzoate

Product 1

HCID 23047222Methyl 2-hydroxy-5-benzylideneaminobenzoateYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 2-hydroxy-5-aminobenzoate (43.6 g, 0.261 mole) was dissolved in benzaldehyde (26.6 ml, 0.26 mole) by heating to 100° C. for 10 minutes and cooled with ice-water after which 95% ethanol (40 ml) was added, and the resulting crystalline material was isolated by filtration. The product was recrystallized from 96% ethanol to give the title compound (45.6 g, 69%), m.p. 58°-59° C. Found (Calc. for C15H13NO3) C 70.60 (70.58), H 5.06 (5.10), N 5.50 (5.49).

Workup

  1. additionwas added
  2. customthe resulting crystalline material was isolated by filtration
  3. customThe product was recrystallized from 96% ethanol

Sources & evidence

ORD record
ord-5c0ab7e86b09447fa2774747c2082aad
Source dataset
uspto-grants-1990_06
Patent number
US04933330

Reaction notes

Loading…