Acetic Anhydride → Methyl 2-acetoxy-5-benzylideneaminobenzoate

HRID 2107010Notes

Reaction equation

HRID 2107010 reaction equation
[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].[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([O: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])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23047222Methyl 2-hydroxy-5-benzylideneaminobenzoate

Product 1

HCID 23047224Methyl 2-acetoxy-5-benzylideneaminobenzoateYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 2-hydroxy-5-benzylideneaminobenzoate (23.5 g, 92.2 mmole) was dissolved in pyridine (50 ml) and acetic anhydride (11 ml) was added after which the reaction mixture was left at room temperature for 48 hours and evaporated to dryness, in vacuo. The remaining material was recrystallized from hexane to give the title compound (13.4 g, 49%), m.p. 101°-103° C. Found (Calc. for C17H15NO4) C 68.57 (68.69), H 4.98 (5.05) N 4.80 (4.71).

Workup

  1. customevaporated to dryness, in vacuo
  2. customThe remaining material was recrystallized from hexane

Sources & evidence

ORD record
ord-1c4b1bb63d874561a6db322f52de952c
Source dataset
uspto-grants-1990_06
Patent number
US04933330

Reaction notes

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