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

HRID 858156노트

반응식

HRID 858156 반응식
[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

참가 물질

4

반응물 2

HCID 24638Chlorosulfonic acidHCID 178515546HCID 178515546, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-46c08dfe89f04b7a94dd10067e7aa0ca
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148236B2

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