7-methyl-6-nitro-1H-indole → 7-methyl-1H-indol-6-amine

HRID 1275656Notes

Reaction equation

HRID 1275656 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-])=O)=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2>[Pd].C(O)C>[NH2:11][C:3]1[C:2]([CH3:1])=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 158963777-methyl-6-nitro-1H-indole

Product 1

HCID 158963787-methyl-1H-indol-6-amineYield 76.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A degassed suspension of 7-methyl-6-nitroindole (1.5 g, 8.5 mmol) and catalytic 10% palladium on carbon in ethanol (75 mL) is placed under an atmosphere of hydrogen at 50 p.s.i. for 7 hours. The reaction mixture is filtered through Celite and the mixture concentrated by rotary evaporation. The crude residue is purified via silica gel column chromatography using 20% isopropanol/hexanes as the eluting solvent. The product containing fractions are combined and the solvents removed by rotary evaporation to yield 0.95 g of 6-amino-7-methylindole as a light brown solid (76% yield).

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. concentrationthe mixture concentrated by rotary evaporation
  3. customThe crude residue is purified via silica gel column chromatography
  4. additionThe product containing fractions
  5. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-d2a03392bdb94c01a270bc30d39bf796
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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