Water → 3-(1H-Indol-7-YL)propanenitrile

HRID 866029Notes

Reaction equation

HRID 866029 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-])=O)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=O.[CH3:15]OC(OC)N(C)C.[NH:23]1CCC[CH2:25][CH2:24]1.O>CN(C)C=O>[C:24]([CH2:25][CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:4]2[C:3]=1[NH:12][CH:15]=[CH:5]2)#[N:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 78373Dimethylformamide dimethyl acetalHCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl ester

Product 1

HCID 199591053-(1H-Indol-7-YL)propanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 3-methyl-2-nitrobenzoate (43 g, 0.22 mole), dimethylformamide dimethyl acetal (52.5 g, 0.44 mole) and piperidine (18.7 g, 0.22 mole) in dimethylformamide (120 ml) is heated under reflux for 24 hours, cooled and poured into water to give the crude product.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperaturecooled

Sources & evidence

ORD record
ord-09e2006741c7442ab92e9cfd1e2386c3
Source dataset
uspto-grants-1996_10
Patent number
US05569764

Reaction notes

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