(2-tert-butyl-5-nitro-1H-indol-7-yl)methanol → (5-amino-2-tert-butyl-1H-indol-7-yl)methanol

HRID 1908440Notes

Reaction equation

HRID 1908440 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][C:8]=2[CH2:17][OH:18])([CH3:4])([CH3:3])[CH3:2]>[Ni].CO>[NH2:14][C:10]1[CH:11]=[C:12]2[C:7](=[C:8]([CH2:17][OH:18])[CH:9]=1)[NH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:13]2

Participants

4

Reactant 1

HCID 59129235(2-tert-butyl-5-nitro-1H-indol-7-yl)methanol

Product 1

HCID 59129268(5-amino-2-tert-butyl-1H-indol-7-yl)methanolYield 97.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2-tert-butyl-5-nitro-1H-indol-7-yl)methanol (4.0 g, 16 mmol) and Raney Nickel (400 mg) in CH3OH (100 mL) was stirred for 5 g at room temperature under H2. The catalyst was filtered off through a celite pad and the filtrate was evaporated under vacuum to give (5-amino-2-tert-butyl-1H-indol-7-yl)methanol (3.4 g, 80%). 1H NMR (CDCl3, 400 MHz) δ 8.53 (br s, 1H), 6.80 (d, J=2.0 Hz, 1H), 6.38 (d, J=1.6 Hz, 1H), 4.89 (s, 2H), 1.37 (s, 9H).

Workup

  1. filtrationThe catalyst was filtered off through a celite pad
  2. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-2b338721136b424cab9e96ac646e9499
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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