Water → 2-(1-methyl-1H-indol-7-yl)acetamide

HRID 2215745

반응식

HRID 2215745 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]#[N:13])[CH:4]=[CH:3]1.[OH-:14].[K+].O>C(O)(C)(C)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]([NH2:13])=[O:14])[CH:4]=[CH:3]1

참가 물질

5

반응물 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 114126242-(1-Methyl-1H-indol-7-yl)acetonitrile

생성물 1

HCID 114353972-(1-methyl-1H-indol-7-yl)acetamide수율 65.5%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

A slurry of (1-methyl-1H-indol-7-yl)-acetonitrile (137 mmol, crude material prepared as described above) in tert-butanol (240 mL) was heated to reflux, KOH (85%, 88.3 g, 1.57 mol) was added and mixture was stirred at reflux for 15 minutes. H2O (1 mL) was introduced and the mixture was heated at reflux for an additional 5 minutes. The solution was allowed to cool, decanted, and diluted with EtOAc (1 L) and H2O. The two layers were separated and the organic solution was washed with H2O and brine. The crude solution was dried (MgSO4), filtered and concentrated to an off-white solid. Trituration with refluxing ether gave the title compound (16.90 g, 65% from 1H-indole-7-carboxaldehyde). 1H NMR (400 MHz, DMSO-d6) 3.87 (s, 2H), 4.03 (s, 3H), 6.39 (d, J=3.2 Hz, 1H), 6.83–7.01 (m, 3H), 7.20 (d, J=3.3 Hz, 1H), 7.30–7.46 (m, 2H). MS (electrospray, m/z) 189.0 (M++1). Anal. Calcd for C11H12N2O: C, 70.19; H, 6.43; N, 14.88. Found: C, 70.03; H, 6.41; N, 14.63.

후처리

  1. temperatureto reflux
  2. temperatureat reflux for 15 minutes
  3. temperaturethe mixture was heated
  4. temperatureat reflux for an additional 5 minutes
  5. temperatureto cool
  6. customdecanted
  7. additiondiluted with EtOAc (1 L) and H2O
  8. customThe two layers were separated
  9. washthe organic solution was washed with H2O and brine
  10. dry with materialThe crude solution was dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated to an off-white solid

출처 및 근거

ORD 기록
ord-1b0df4b0a8f14c6c9981a1105b3f2c6c
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109229B2

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