Acetic Anhydride → 2-acetoxymethyl-5-methoxy-N-(3-pyridylmethyl)benzamide

HRID 1609596

Reaction equation

HRID 1609596 reaction equation
[OH:1][CH2:2][C:3]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:4]=1[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:6].C(N(CC)CC)C.[C:28](OC(=O)C)(=[O:30])[CH3:29]>C(Cl)Cl>[C:28]([O:1][CH2:2][C:3]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:4]=1[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:6])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 200820052-hydroxymethyl-5-methoxy-N-(3-pyridylmethyl)benzamide

Product 1

HCID 200820032-acetoxymethyl-5-methoxy-N-(3-pyridylmethyl)benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 710 mg of 2-hydroxymethyl-5-methoxy-N-(3-pyridylmethyl) benzamide and 317 mg of triethylamine in 10 ml of methylene chloride was chilled at 0° C., mixed with 320 mg of acetic anhydride and stirred at room temperature for 15 hours. The reaction mixture was washed with water and saturated brine in order. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo to give 820 mg of the titled compound.

Workup

  1. washThe reaction mixture was washed with water and saturated brine in order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6561ddaba5174c80b382cf9c5f8839d1
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Linked notes

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