Water → N-(2-Phenyl-1H-indol-6-yl)isobutyramide

HRID 1896791Notes

Reaction equation

HRID 1896791 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[C:11]([NH2:16])[CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](Cl)(=[O:21])[CH:18]([CH3:20])[CH3:19].O>N1C=CC=CC=1>[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[C:11]([NH:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[CH:10]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 62325Isobutyryl chlorideHCID 114131282-phenyl-1H-indol-6-amine

Product 1

HCID 67332821N-(2-Phenyl-1H-indol-6-yl)isobutyramideYield 21%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-phenyl-1H-indol-6-amine (54 mg, 0.26 mmol) in pyridine (2 mL) at room temperature was added isobutyryl chloride (30 μL, 0.29 mmol). The resulting mixture was stirred at room temperature for 2 days. When water was added, a precipitate was formed. This solid was recrystallised from hot ethyl acetate to afford 15 mg (21%) of the title compound (LCMS RT=6.27 min, MH+ 279.0)

Workup

  1. customa precipitate was formed
  2. customThis solid was recrystallised from hot ethyl acetate

Sources & evidence

ORD record
ord-714587ebf743428d93f31b93ebc4f28e
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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