Water → 5-methoxy-1-methyl-1H-indole-3-carbonitrile

HRID 1765585Notes

Reaction equation

HRID 1765585 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[CH:13]=O.Cl.[NH2:16]O.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]#[N:16]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 9259735-methoxy-1-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 224772695-methoxy-1-methyl-1H-indole-3-carbonitrileYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Methoxy-1-methyl-1H-indole-3-carbaldehyde [76 g, Reference Example 2(a)] and hydroxylamine hydrochloride (55.9 g) were stirred together in dimethylformamide (900 mL) under reflux for 1 hour. The mixture was allowed to cool, then poured into water and then extracted with ethyl acetate. The combined extracts were washed with water then evaporated to give the title compound (53 g) as a pale brown solid, m.p. 100–104° C. 1H NMR [(CD3)2SO]: δ 8.17 (1H, s); 7.54 (1H, d, J=9.0 Hz); 7.09 (1H, d, J=2.4 Hz); 6.97 (1H, dd, J=9.0 and 2.4 Hz); 3.82 and 3.84 (6H, s).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with water
  5. customthen evaporated

Sources & evidence

ORD record
ord-b7e3ae864fb94c3f93185da9fa44c6de
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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