Dichloromethane → 4-Chloro-7-(trifluoromethyl)quinoline

HRID 1678307Notes

Reaction equation

HRID 1678307 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:16]CCl>O=P(Cl)(Cl)Cl>[Cl:16][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 178516425HCID 178516425, compound

Product 1

HCID 676684-Chloro-7-(trifluoromethyl)quinoline

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 4-hydroxy-7-trifluoromethylquinoline (1 g) in dichloromethane (10 mL) and POCl3 (1 mL) was refluxed for half an hour. Then the reaction mixture was quenched with water (80 mL) and sodium bicarbonate to pH 7. The aqueous solution was extracted with dichloromethane (2×60 mL). The organic layers were combined, dried, evaporated to give 4-chloro-7-trifluoromethylquinoline. LCMS: ret. time: 31.51 min.; purity: 100%; MS (m/e): 232 (MH+).

Workup

  1. customThen the reaction mixture was quenched with water (80 mL) and sodium bicarbonate to pH 7
  2. extractionThe aqueous solution was extracted with dichloromethane (2×60 mL)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-961a5ef2bac34596b34ad7bce66deb06
Source dataset
uspto-grants-2011_08
Patent number
US08008501B2

Reaction notes

Loading…