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

HRID 1835204Notes

Reaction equation

HRID 1835204 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-e00a8ed1e43f4b96bd007af8bf64a463
Source dataset
uspto-grants-2004_08
Patent number
US06770643B2

Reaction notes

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