Hydrazine → 5-Amino-2-methylindole

HRID 2297811Notes

Reaction equation

HRID 2297811 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([N+:11]([O-])=O)=[CH:6][CH:5]=2.NN>[Pd].C(O)C>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([NH2:11])=[CH:6][CH:5]=2

Participants

5

Reactant 2

HCID 9321HydrazineHCID 2803132-Methyl-5-nitro-1H-indole

Product 1

HCID 27339925-Amino-2-methylindole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-methyl-5-nitroindole (200 mg, 1.13 mmol) and palladium on carbon (20 mg, 10%) in 10 mL of ethanol was added hydrazine (100 mg, 3.4 mmol) and heated at 80° C. for 16 hours. The reaction mixture was filtered through celite and concentrated in vacuo to provide a red-brown solid which was used without further purification. RP18-HPLC RT: 1.278 minutes; API MS: 147.1 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customto provide a red-brown solid which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-62a750b1942f4b51aefb8aba8a14e9bb
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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