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

HRID 2215745

Reaktionsgleichung

Reaktionsgleichung von HRID 2215745
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 114353972-(1-methyl-1H-indol-7-yl)acetamideAusbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1b0df4b0a8f14c6c9981a1105b3f2c6c
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109229B2

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