5-tert-butyl-6-nitro-1H-indole → HCID 57470208, compound

HRID 2038110Notes

Reaction equation

HRID 2038110 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-])=O)[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]>[Ni].CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[NH2:14])[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 574702075-tert-butyl-6-nitro-1H-indole

Product 1

HCID 57470208HCID 57470208, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

Raney Nickel (3 g) was added to 5-tert-butyl-6-nitro-1H-indole (15 g, 67 mmol) in methanol (100 mL). The mixture was stirred under hydrogen (1 atm) at 30° C. for 3 h. The catalyst was filtered off. The filtrate was dried over Na2SO4 and concentrated. The crude dark brown viscous oil was purified by column chromatography (10-20% ethyl acetate/petroleum ether) to give 5-tert-butyl-1H-indol-6-ylamine as a gray solid (11 g, 87%). NMR (300 MHz, DMSO-d6) δ 10.3(br s, 1H), 7.2(s, 1H), 6.9(m, 1H), 6.6(s, 1H), 6.1(m, 1H), 4.4(br s, 2H), 1.3 (s, 9H).

Workup

  1. filtrationThe catalyst was filtered off
  2. dry with materialThe filtrate was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude dark brown viscous oil was purified by column chromatography (10-20% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-667925c704b94fe699603b10e095af90
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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