Pyridine → HCID 69432694, compound

HRID 1269922Notes

Reaction equation

HRID 1269922 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([F:16])[C:10]=1[CH3:17].N1C=CC=CC=1.[C:24](OCC)(=[O:26])[CH3:25]>>[C:1]([O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:24](=[O:26])[CH3:25])=[C:10]([CH3:17])[C:11]=1[F:16])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 22933920HCID 22933920, compound

Product 1

HCID 69432694HCID 69432694, compoundYield 15%

Conditions

Temperature
65 °C

Procedure

Acetic anhydride (4.49 ml, 47.6 mmol) was added dropwise to a solution of 4-amino-2-fluoro-3-methylphenol (2.80 g, 1.91 mmol) and pyridine (3.53 ml, 43.6 mmol) in ethyl acetate (60 ml) at room temperature, and the resulting mixture was slowly heated to 65° C. and stirred for 45 minutes while being maintained at this temperature. The resulting reaction solution was cooled to room temperature and partitioned by the use of water and ethyl acetate to find that an insoluble material was present. The insoluble material was collected by filtration and dried to obtain 4-(acetylamino)-2-fluoro-3-methylphenyl acetate (679 mg, 15%). The filtrate was concentrated and then extracted with chloroform to obtain a crude product, and the crude product was washed with ethyl acetate (8 ml)-hexane (24 ml) by repulping, collected by filtration and then dried to obtain 4-(acetylamino)-2-fluoro-3-methylphenyl acetate (3.54 g, 79%).

Workup

  1. temperaturewhile being maintained at this temperature
  2. customThe resulting reaction solution
  3. temperaturewas cooled to room temperature
  4. custompartitioned by the use of water and ethyl acetate
  5. filtrationThe insoluble material was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c346111204384d03a99155a4b5cc9ea4
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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