Ammonium formate → HCID 15549846, compound

HRID 275784Notes

Reaction equation

HRID 275784 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH3:19])=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>CCO.CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH3:19])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 15549845HCID 15549845, compound

Product 1

HCID 15549846HCID 15549846, compoundYield 82.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of the above nitro compound ( 300 mg, 1.2 mmol) in EtOH (25 mL) and EtOAc (5 mL) was added solid ammonium formate (750 mg, 11.9 mmol) followed by 10% Pd—C (50 mg). The mixture was stirred for 2 h at room temperature, and then filtered through a short pad of diatomaceous earth and washed with EtOH/EtOAc. The filtrate was concentrated to give 1-(4-aminophenyl)-2-methylindol (0.22 g).

Workup

  1. filtrationfiltered through a short pad of diatomaceous earth
  2. washwashed with EtOH/EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a9b2053dfc5243819494b31c01ddf509
Source dataset
uspto-grants-2002_03
Patent number
US06353007B1

Reaction notes

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