Benzaldehyde → Ethyl 2-hydroxy-5-benzylideneaminobenzoate

HRID 2107014Notes

Reaction equation

HRID 2107014 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[OH:1][C:2]1[CH:12]=[CH:11][C:10]([N:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 13445456Ethyl 5-amino-2-hydroxybenzoate

Product 1

HCID 23047228Ethyl 2-hydroxy-5-benzylideneaminobenzoateYield 67%

Conditions

Temperature
100 °C

Procedure

Ethyl 2-hydroxy-5-aminobenzoate (31.8 g, 0.176 mole) was mixed with benzaldehyde (17.8 ml, 0.176 mole), and the mixture was heated to 100° C. for 10 minutes and subsequently cooled with ice-water. The resulting oil was recrystallized from 96% ethanol, with activated carbon, to give the title compound (31.6 g, 67%), m.p. 63°-65° C. Found (Calc. for C16H15NO3) C 71.18 (71.38), H 5.63 (5.58), N 5.22 (5.20).

Workup

  1. customThe resulting oil was recrystallized from 96% ethanol, with activated carbon

Sources & evidence

ORD record
ord-a9ae4075f2c84f2a906151a1c67138b7
Source dataset
uspto-grants-1990_06
Patent number
US04933330

Reaction notes

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