Phosphorus oxychloride → 2-Chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester

HRID 1949155Notes

Reaction equation

HRID 1949155 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](O)=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:24]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:24])=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470056HCID 178470056, compound

Product 1

HCID 866453402-Chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl esterYield 98.6%

Procedure

4.3 g (14.4 mmol) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester (precursor VVV05) were heated together with 13.3 ml (144.1 mmol) POCl3 for 2 h at 100° C. After cooling to RT the mixture was concentrated to small volume under vacuum. 4.5 g (14.2 mmol, 98%) 2-chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester were obtained as residue.

Workup

  1. concentrationwas concentrated to small volume under vacuum

Sources & evidence

ORD record
ord-49fe3c21595946f4aadd6526fc767872
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

Loading…