Formic Acid → N-(3-acetylphenyl)formamide

HRID 1906839Notes

Reaction equation

HRID 1906839 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[NH2:11][C:12]1[CH:13]=[C:14]([C:18](=[O:20])[CH3:19])[CH:15]=[CH:16][CH:17]=1.C(N(C(C)C)CC)(C)C>ClCCl>[C:18]([C:14]1[CH:13]=[C:12]([NH:11][CH:8]=[O:10])[CH:17]=[CH:16][CH:15]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 74173'-AminoacetophenoneHCID 7918Acetic AnhydrideHCID 81531Diisopropylethylamine

Product 1

HCID 4118677N-(3-acetylphenyl)formamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A 25 ml portion of acetic anhydride was cooled at 0° C. in an ice bath. A 12.5 ml portion of formic acid was added, the mixture was heated at 50° C. for 15 minutes then cooled to 0° C., giving 9.69 g of crude mixed formicacetic anhydride. This anhydride was reacted with 13.52 g of m-aminoacetophenone, 14.21 g of diisopropylethylamine and 800 ml of dichloromethane as described in Example 1, giving 13.27 g of N-(3-acetylphenyl)formamide, mp 100°-102° C.

Workup

  1. temperaturethen cooled to 0° C.
  2. customgiving 9.69 g of crude

Sources & evidence

ORD record
ord-ae8718c8c8f3493bb81041693c457b52
Source dataset
uspto-grants-1987_03
Patent number
US04654347

Reaction notes

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