Acetic Anhydride → Ethyl 2-acetoxy-5-benzylideneaminobenzoate

HRID 2107015Notes

Reaction equation

HRID 2107015 reaction equation
[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].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([O: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])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23047228Ethyl 2-hydroxy-5-benzylideneaminobenzoate

Product 1

HCID 23047223Ethyl 2-acetoxy-5-benzylideneaminobenzoateYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 2-hydroxy-5-benzylideneaminobenzoate (21 g, 78 mmole) was dissolved in pyridine (60 ml) and acetic anhydride (8.9 ml) was added after which the reaction mixture was kept at room temperature for 48 hours, evaporated to dryness in vacuo, and the residue recrystallized from hexane to give the title compound (17.8 g, 73%), m.p. 79°-80° C. Found (Calc. for C18H17NO4) C 69.33 (69.45), H 5.51 (5.47), N 4.57 (4.50).

Workup

  1. customevaporated to dryness in vacuo
  2. customthe residue recrystallized from hexane

Sources & evidence

ORD record
ord-e0729028dcb146fbaadc5cd8b27ca884
Source dataset
uspto-grants-1990_06
Patent number
US04933330

Reaction notes

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