Water → 7-amino-4-methyl-1H-indole-3-carbonitrile

HRID 2355779Notes

Reaction equation

HRID 2355779 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[C:7]([N+:13]([O-])=O)[CH:8]=[CH:9][C:10]=2[CH3:12])[NH:5][CH:4]=1)#[N:2].O>C(OCC)(=O)C.CO.COCCOC.[C].[Pd]>[NH2:13][C:7]1[CH:8]=[CH:9][C:10]([CH3:12])=[C:11]2[C:6]=1[NH:5][CH:4]=[C:3]2[C:1]#[N:2]

Participants

7

Reactant 2

HCID 962WaterHCID 116225274-Methyl-7-nitro-1H-indole-3-carbonitrile

Product 1

HCID 117152477-amino-4-methyl-1H-indole-3-carbonitrileYield 84.8%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After suspending 400 g (1.99 mol) of the 3-cyano-4-methyl-7-nitro-1H-indole obtained in Example 1A in a mixture of 6 L of ethyl acetate and 6 L of methanol, the suspension was subjected to hydrogenation in the presence of 40 g of 10% palladium-carbon at ordinary temperature, 4 atmospheres. After removing the catalyst by filtration, the filtrate was treated with activated carbon and concentrated to give crude crystals. The crude crystals were dissolved in 6 L of 1,2-dimethoxyethane at an external temperature of 60° C., and then 12 L of water was added dropwise. Upon confirming precipitation of crystals, the mixture was stirred for 1.5 hours while cooling in an ice bath and filtered, and the crystals were washed twice with water (1 L). The crystals were air-dried at 50° C. for 16 hours to give 289 g of the title compound (yield: 84.8%).

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. additionthe filtrate was treated with activated carbon
  4. concentrationconcentrated
  5. customto give crude crystals
  6. customprecipitation of crystals
  7. temperaturewhile cooling in an ice bath
  8. filtrationfiltered
  9. washthe crystals were washed twice with water (1 L)
  10. customThe crystals were air-dried at 50° C. for 16 hours

Sources & evidence

ORD record
ord-55fff931669544c3aab53a562443b019
Source dataset
uspto-grants-2010_07
Patent number
US07754894B2

Reaction notes

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