Chlorosulfonic acid → 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

HRID 1969935ノート

反応式

HRID 1969935 の反応式
[O:1]=[C:2]1[C:11]2[NH:12][CH:13]=[CH:14][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.C([C:17]([O-:19])=[O:18])C.[Cl:20][S:21](O)(=[O:23])=[O:22]>>[Cl:20][S:21]([C:7]1[CH:6]=[CH:5][C:4]2[NH:3][C:2](=[O:1])[C:11]3[NH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[C:10]=3[C:9]=2[CH:8]=1)(=[O:23])=[O:22]

参加物

3

反応物 2

HCID 24638Chlorosulfonic acidHCID 86627461HCID 86627461、化合物

生成物 1

HCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid収率 60%

反応条件

温度
0 °C

実験手順

85 mg (0.33 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate as prepared in the preceding synthesis 1 is added in the space of 90 minutes to 106 μL (1.65 mmol) of chlorosulfonic acid cooled to 0° C. on an ice bath. On completion of addition, the solution is stirred for 1 hour at room temperature then 3 hours at 70° C. The reaction mixture is cooled to room temperature then poured into ice water (20 mL). The mixture is stirred for 15 minutes then the solid is filtered, and taken up in methanol/toluene mixture. The solvents are evaporated to give 64 mg (60%) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid in the form of a beige solid.

後処理

  1. additionOn completion of addition
  2. custom3 hours
  3. customat 70° C
  4. temperatureThe reaction mixture is cooled to room temperature
  5. stirringThe mixture is stirred for 15 minutes
  6. filtrationthe solid is filtered
  7. customThe solvents are evaporated

出典と根拠

ORDレコード
ord-5b664e8aa71a43aeb228da7083bce479
出典データセット
uspto-grants-2013_04
特許番号
US08426437B2

反応ノート

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