Acetic Anhydride → HCID 59834294, compound

HRID 271068Notes

Reaction equation

HRID 271068 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:10]=[C:9]([NH2:11])[C:8]([CH3:12])=[CH:7][N:6]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:10]=[C:9]([NH:11][C:18](=[O:20])[CH3:19])[C:8]([CH3:12])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 59834331HCID 59834331, compound

Product 1

HCID 59834294HCID 59834294, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,4-difluorophenoxy)-5-methylpyridin-4ylamine (3.6 g) in 80 mL of methylene chloride was added 4.7 g of acetic anhydride. The mixture was heated for 24 hours on a steam bath and then poured onto 200 mL of 5% aqueous sodium carbonate. The aqueous solution was extracted with methylene chloride. The organic layers were combined, dried and concentrated to give 4.2 g of N-[2-(2,4-difluorophenoxy)-5-methylpyridin-4-yl]acetamide (99% yield). Mass. Spec. M+H=279.

Workup

  1. temperatureThe mixture was heated for 24 hours on a steam bath
  2. extractionThe aqueous solution was extracted with methylene chloride
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-20b2c7969262460f85c69f58bf1c90c8
Source dataset
uspto-grants-2008_11
Patent number
US07452880B2

Reaction notes

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