Phosphorus oxychloride → 4-Chloro-5-fluoro-2-(2-fluorophenyl)-3-methylquinoline

HRID 1431277Notes

Reaction equation

HRID 1431277 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][CH3:10].[NH2:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:14]=1[C:15](O)=O.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:15]1[C:14]2[C:13](=[CH:21][CH:20]=[CH:19][C:18]=2[F:22])[N:12]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:9]=1[CH3:10]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 5211422-Amino-6-fluorobenzoic acidHCID 5793991-(2-Fluorophenyl)propan-1-one

Product 1

HCID 596314454-Chloro-5-fluoro-2-(2-fluorophenyl)-3-methylquinoline

Procedure

Prepared according to Procedure J using 1-(2-fluorophenyl)propan-1-one and 2-amino-6-fluorobenzoic acid in phosphorous oxychloride to afford a colorless solid upon purification by chromatography on silica gel. Mass Spectrum (ESI) m/e=290.0 (M+1).

Workup

  1. customPrepared
  2. customto afford a colorless solid
  3. customupon purification by chromatography on silica gel

Sources & evidence

ORD record
ord-2307e20cd17b4375b22da575d0c15d71
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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