2-Amino-5-chlorobenzoic acid → 4,6-Dichloro-2-(2-fluorophenyl)-3-methylquinoline

HRID 1431229Notes

Reaction equation

HRID 1431229 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](O)=O.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=O)[CH2:20][CH3:21].P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[C:8]([Cl:11])[CH:7]=2)[N:1]=[C:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[F:12])[C:20]=1[CH3:21]

Participants

4

Reactant 3

HCID 124762-Amino-5-chlorobenzoic acidHCID 24813Phosphorus oxychlorideHCID 5793991-(2-Fluorophenyl)propan-1-one

Product 1

HCID 596313274,6-Dichloro-2-(2-fluorophenyl)-3-methylquinoline

Procedure

Prepared according to Procedure J using 2-amino-5-chlorobenzoic acid (1.5 equiv.) and 1-(2-fluorophenyl)propan-1-one (1 equiv.) in phosphorous oxychloride to afford 4,6-dichloro-2-(2-fluorophenyl)-3-methylquinoline upon purification by chromatography on silica gel. Mass Spectrum (ESI) m/e=306.0 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-dfb14b945b9645f59ddd255130b5b720
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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