Sulfuric Acid → 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrile

HRID 641877Notes

Reaction equation

HRID 641877 reaction equation
OS(O)(=O)=O.[CH3:6][N:7]1[CH2:12][CH:11]=[C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([NH2:24])=O)[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8]1>C(O)C>[CH3:6][N:7]1[CH2:8][CH:9]=[C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:24])[CH:20]=3)[NH:15][CH:14]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 149732133-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carboxamide

Product 1

HCID 149732163-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrileYield 20.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

H2SO4 (0.1 mL) was added to a solution of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carboxamide (130 mg, 0.41 mmol) in ethanol (4 mL) and the resulting solution was stirred at room temperature for 1 hour. Filtration and subsequent concentration afforded 20 mg (18.6%) of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrile as a white solid.

Workup

  1. filtrationFiltration and subsequent concentration

Sources & evidence

ORD record
ord-9fe0ecaf2f484157b4bfd3ede10be502
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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