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

HRID 858156Notes

Reaction equation

HRID 858156 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>ClCCl>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:13]([Cl:12])(=[O:15])=[O:14])[CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 178515546HCID 178515546, compound

Product 1

HCID 534146522-Oxo-1,2-dihydroquinoline-6-sulfonyl chlorideYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice bath cooled stirred slurry of 2-hydroxyquinoline (30.5 g, 0.210 mol) in dichloromethane (300 cm3) was added chlorosulphonic acid (70 cm3, 1.05 mol) in 4 equal sized batches. This was left to stir at room temperature for 2 days then slowly poured onto crushed ice. Large amount of a white solid formed in the lower chlorinated layer. This was filtered off and dried in vacua to yield 2-Oxo-1,2-dihydro-quinoline-6-sulfonyl chloride as a dry white solid (36.3 g); δH (300 MHz; D6 DMSO) 6.51–6.59 (1H, m, 1×Ar—H), 7.29–7.34 (1H, m, Ar—H), 7.71–7.79 (1H, m, Ar—H), 7.90–7.96 (1H, m, Ar—H) and 8.00–8.06 (1H, m, Ar—H); LCMS retention time ˜3.43 min, m/z (FIANEG) 241.9 [Cl35(M)−, 100%] and 244.0 [Cl37(M)−, 33%]. NMR and LCMS showed that this material contained some starting material as a minor impurity but no further purification was performed.

Workup

  1. temperatureTo an ice bath cooled
  2. waitThis was left
  3. additionthen slowly poured
  4. customonto crushed ice
  5. customLarge amount of a white solid formed in the lower chlorinated layer
  6. filtrationThis was filtered off
  7. customdried in vacua

Sources & evidence

ORD record
ord-46c08dfe89f04b7a94dd10067e7aa0ca
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

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