Chlorosulfonic acid → 2-Oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonyl chloride

HRID 1829899Notes

Reaction equation

HRID 1829899 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5](=[O:13])[CH:4]=1.[Cl:16][S:17](O)(=[O:19])=[O:18]>>[O:13]=[C:5]1[CH:4]=[C:3]([C:2]([F:1])([F:14])[F:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:17]([Cl:16])(=[O:19])=[O:18])[CH:11]=2)[NH:6]1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 27593472-Hydroxy-4-(trifluoromethyl)quinoline

Product 1

HCID 220553102-Oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonyl chlorideYield 41%

Conditions

Temperature
140 °C

Procedure

4-Trifluoromethyl-1H-quinolin-2-one (5.00 g, 23.5 mmol) was treated with ClSO3H (3.1 mL, 47.0 mmol) at 0° C. The mixture was then heated with stirring to 140° C. for 7 hours. On cooling, ice-cold H2O (50 mL) was added. The solid produced was collected and dried to give the title compound (2.93 g, 41%): δH (CDCl3)=7.20 (s, 1H), 7.60 (d, 1H), 8.20 (dd, 1H), 8.50 (d, 1H).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureOn cooling
  3. customThe solid produced
  4. customwas collected
  5. customdried

Sources & evidence

ORD record
ord-ab43a3d9ccc442d3ad5cbb40906e2f78
Source dataset
uspto-grants-2006_06
Patent number
US07064207B2

Reaction notes

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