Acetic Anhydride → N-[2-(Benzyloxy)-5-(pyridine-2-carbonyl)phenyl]acetamide

HRID 1287844Notes

Reaction equation

HRID 1287844 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:11]([NH2:23])[CH:10]=1)=[O:8].[C:24](OC(=O)C)(=[O:26])[CH3:25].[OH-].[Na+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:11]([NH:23][C:24](=[O:26])[CH3:25])[CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 53880974[3-Amino-4-(benzyloxy)phenyl](pyridin-2-yl)methanone

Product 1

HCID 53916260N-[2-(Benzyloxy)-5-(pyridine-2-carbonyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.0 g (32.8 mmol) of 3-amino-4-benzyloxyphenyl 2-pyridyl ketone and 40 ml of acetic anhydride is heated on a steam bath for 1 hour. The reaction is concentrated in vacuo to give a residue which is suspended in water and made basic with 10% NaOH. The aqueous phase is extracted with ether and the dried extracts are evaporated to give 3-acetamido-4-benzyloxyphenyl 2-pyridyl ketone.

Workup

  1. temperatureis heated on a steam bath for 1 hour
  2. concentrationThe reaction is concentrated in vacuo
  3. customto give a residue which
  4. extractionThe aqueous phase is extracted with ether
  5. customthe dried extracts are evaporated

Sources & evidence

ORD record
ord-f3f9ebe34c5548768718f41339eb1228
Source dataset
uspto-grants-1976_10
Patent number
US03985887

Reaction notes

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