Thionyl Chloride → 1H-indole-3-carbohydrazide

HRID 1697443노트

반응식

HRID 1697443 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.S(Cl)(Cl)=O.O.[NH2:18][NH2:19]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([NH:18][NH2:19])=[O:12])=[CH:2]1

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 24654Hydrazine hydrate (1:1)HCID 69867Indole-3-Carboxylic Acid

생성물 1

HCID 271991H-indole-3-carbohydrazide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Indole-3-carboxylic acid (500 mg, 3.1 mmol) was stirred at room temperature with thionyl chloride (5 mL, 68 mmol) for 20 hours. The solution was concentrated under vacuum and the residue was taken up in ether (10 mL) and concentrated to dryness (repeated three times) to ensure removal of the thionyl chloride. The resulting solid was dissolved in ether (5 mL) and added to an ice cooled solution of hydrazine hydrate (600 mg, 12 mmol) in tetrahydrofuran (5 mL). After 30 minutes, the solid was collected by filtration, washed with 5% NaOH and water, and dried under vacuum at 50° C. The crude hydrazide was recrystallized from 95% ethanol to provide the title compound. 1H NMR (300 MHz, CD3OD) δ 7.11-7.22 (m, 2 H), 7.42 (dd, J=7, 2 Hz, 1 H), 7.83 (s, 1 H), 8.02-8.08 ppm (m, 1 H); MS (DCI/NH3) m/z 176 (M+H)+.

후처리

  1. concentrationThe solution was concentrated under vacuum
  2. concentrationconcentrated to dryness (repeated three times)
  3. customremoval of the thionyl chloride
  4. dissolutionThe resulting solid was dissolved in ether (5 mL)
  5. filtrationthe solid was collected by filtration
  6. washwashed with 5% NaOH and water
  7. customdried under vacuum at 50° C
  8. customThe crude hydrazide was recrystallized from 95% ethanol

출처 및 근거

ORD 기록
ord-41c6a027f4aa45b89a94eb2eb72bfc1b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163915B2

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