Ammonia → 4'-Fluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxamide

HRID 442273Notes

Reaction equation

HRID 442273 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[OH:17].[NH3:19]>>[OH:17][C:5]1[CH:6]=[CH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:9][C:4]=1[C:3]([NH2:19])=[O:2]

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 21416429Methyl 4'-fluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 214164704'-Fluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxamide

Procedure

A mixture of 5.3 grams of methyl-2-hydroxy-5-(4'-fluorophenyl)-benzoate and 20 ml. of liquid ammonia is reacted in a bomb at 100° C. for 4 hours. After cooling the bomb is opened and the ammonia allowed to evaporate. The residue is then recrystallized from benzene to yield 2-hydroxy-5-(4'-fluorophenyl)-benzamide (m.p. 206° - 207° C.).

Workup

  1. temperatureAfter cooling the bomb
  2. customto evaporate
  3. customThe residue is then recrystallized from benzene

Sources & evidence

ORD record
ord-82e3831daaf14367b10a16b9af5ae4c5
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

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