Anthranilic Acid → 4-Chloro-2-(2-fluorophenyl)-3-methylquinoline

HRID 1431288Notes

Reaction equation

HRID 1431288 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=O.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=O)[CH2:19][CH3:20].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:1]=[C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[F:11])[C:19]=1[CH3:20]

Participants

4

Reactant 3

HCID 227Anthranilic AcidHCID 24813Phosphorus oxychlorideHCID 5793991-(2-Fluorophenyl)propan-1-one

Product 1

HCID 596311684-Chloro-2-(2-fluorophenyl)-3-methylquinoline

Procedure

Prepared according to Procedure J, using 2-aminobenzoic acid (14.6 g, 106 mmol) and 1-(2-fluorophenyl)propan-1-one (10.78 g, 70.8 mmol) in phosphorous oxychloride (35.00 mL) to afford product as a colorless solid upon purification by chromatography on silica gel, eluting with EtOAc gradient in hexane. Mass Spectrum (ESI) m/e=272.0 (M+1).

Workup

  1. customPrepared
  2. customto afford product as a colorless solid
  3. customupon purification by chromatography on silica gel
  4. washeluting with EtOAc gradient in hexane

Sources & evidence

ORD record
ord-f5a45899eda243b6ba4cd244387a24ba
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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