HCID 20406152, compound → Methanone, (2-amino-5-methylphenyl)(4-fluorophenyl)-

HRID 2164305Notes

Reaction equation

HRID 2164305 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[NH:15]C(=O)C)=[O:7])=[CH:4][CH:3]=1>C(O)C.Cl>[NH2:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[C:6]([C:5]1[CH:19]=[CH:20][C:2]([F:1])=[CH:3][CH:4]=1)=[O:7]

Participants

4

Reactant 1

HCID 20406152HCID 20406152, compound

Product 1

HCID 10966280Methanone, (2-amino-5-methylphenyl)(4-fluorophenyl)-Yield 61.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 119 g (0.44 mole of N-[2-(4-fluorobenzoyl)-4-methylphenyl]acetamide in 500 ml of 95% ethanol and 300 ml of 6N hydrochloric acid was heated at reflux for 16 hr. The solvents were removed on a roto-evaporator and the residue obtained was partitioned between concentrated ammonium hydroxide and benzene. The organic layer was concentrated and the new residue was chromatographed on silica gel, eluting with 10% ethyl acetate in hexane. The product fractions were concentrated and the residue was crystallized from a mixture of cyclohexane and hexane to give 56.3 g (61.5%) of the titled compound as bright yellow crystals, m.p. 70.0°-71.5° C.

Workup

  1. temperatureat reflux for 16 hr
  2. customThe solvents were removed on a roto-evaporator
  3. customthe residue obtained
  4. customwas partitioned between concentrated ammonium hydroxide and benzene
  5. concentrationThe organic layer was concentrated
  6. customthe new residue was chromatographed on silica gel
  7. washeluting with 10% ethyl acetate in hexane
  8. concentrationThe product fractions were concentrated
  9. customthe residue was crystallized from a mixture of cyclohexane and hexane

Sources & evidence

ORD record
ord-ce1a0d64d9574e01bf7a2c3c022d8ff6
Source dataset
uspto-grants-1985_03
Patent number
US04503073

Reaction notes

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