Ammonium Chloride → 1-methyl-1H-indol-6-amine

HRID 1886952Notes

Reaction equation

HRID 1886952 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[CH:4]=[CH:3]1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[CH:4]=[CH:3]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 106073591-Methyl-6-nitro-1H-indole

Product 1

HCID 105347991-methyl-1H-indol-6-amineYield 40.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
70 °C

Procedure

1-methyl-6-nitro-1H-indole (90 mg, 0.51 mmol), ammonium chloride (55 mg, 1.02 mmol) and iron powder (143 mg, 2.55 mmol) were suspended in ethanol/water (2 mL/1 mL) and heated at 70° C. for 2 h. After cooling, the solution was filtrated through a pad of Celite®, which was washed with ethanol. Ethyl acetate was added to the filtrate and the organic layer was washed with water twice. The combined organic layers were dried over anhydrous MgSO4 and evaporated to afford 30 mg (37%) of the title compound

Workup

  1. temperatureAfter cooling
  2. filtrationthe solution was filtrated through a pad of Celite®, which
  3. washwas washed with ethanol
  4. additionEthyl acetate was added to the filtrate
  5. washthe organic layer was washed with water twice
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-011eabb246ba4d59aaaa47f6f1982497
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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