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

HRID 375683

Reaction equation

HRID 375683 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-99b69e106a784f89aab343a351df0e89
Source dataset
uspto-grants-1996_01
Patent number
US05486612

Linked notes

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