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

HRID 858156ノート

反応式

HRID 858156 の反応式
[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

参加物

4

反応物 2

HCID 24638Chlorosulfonic acidHCID 178515546HCID 178515546、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-46c08dfe89f04b7a94dd10067e7aa0ca
出典データセット
uspto-grants-2006_12
特許番号
US07148236B2

反応ノート

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