Hydrochloric Acid → 2,3-dihydro-1H-indole-5-sulfonamide

HRID 528822

反応式

HRID 528822 の反応式
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)C.Cl>CO>[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH2:16])(=[O:14])=[O:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 8042081-Acetylindoline-5-sulfonamide2 回

生成物 1

HCID 80272522,3-dihydro-1H-indole-5-sulfonamide収率 87.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a suspension of 1-acetylindoline-5-sulfonamide (Intermediate 52A, 1.00 g, 4.16 mmol) in MeOH (12.0 mL) was added conc. HCl (1.7 mL, 20.8 mmol). The resulting reaction mixture was stirred at room temperature for 18 h and then at 80° C. for 2 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The brown residue was dissolved in water and the solution was adjusted to a pH of 7-8 with 1 N aq. NaOH solution. The mixture was then extracted with EtOAc (2×), and the combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (720 mg, 87%) as a light brown solid. 1H NMR (DMSO-d6) δ 7.42-7.38 (m, 2H), 6.86 (s, 2H), 6.47 (d, J=8.1 Hz, 1H), 6.24-6.22 (m, 1H), 3.53-3.50 (m, 2H), 2.98-2.95 (m, 2H); MS(ESI+) m/z 199.1 (M+H)+.

後処理

  1. customThe resulting reaction mixture
  2. waitat 80° C. for 2 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. dissolutionThe brown residue was dissolved in water
  6. extractionThe mixture was then extracted with EtOAc (2×)
  7. dry with materialthe combined organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1a020e9bcd98428989d450a57ef4cf16
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

関連ノート

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