ethyl 1-methyl-5-nitro-1H-indole-2-carboxylate → Ethyl 5-amino-1-methyl-1H-indole-2-carboxylate

HRID 2085876Notes

Reaction equation

HRID 2085876 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>[Pd].C(OCC)(=O)C>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4]2

Participants

4

Reactant 1

HCID 10538482ethyl 1-methyl-5-nitro-1H-indole-2-carboxylate

Product 1

HCID 11424506Ethyl 5-amino-1-methyl-1H-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Preferred alternative B. A mixture of ethyl 1-methyl-5-nitro-1H-indole-2-carboxylate (150.0 g), from step (a) or commercial sources, and 10% palladium on carbon catalyst (50% wet) (15.0 g) in ethyl acetate (1800 mL) was hydrogenated at 3 bar at 30° C. for 8 hours. The mixture was then filtered and the solids washed with ethyl acetate (300 mL). The combined filtrate and washings were partially azeotropically dried at reflux and then concentrated to 800 mL to give a solution of product ethyl 5-amino-1-methyl-1H-indole-2-carboxylate in ethyl acetate.

Workup

  1. filtrationThe mixture was then filtered
  2. washthe solids washed with ethyl acetate (300 mL)
  3. customThe combined filtrate and washings were partially azeotropically dried
  4. temperatureat reflux
  5. concentrationconcentrated to 800 mL

Sources & evidence

ORD record
ord-285e60f4b7df47dba49dfbe9d5fed9fb
Source dataset
uspto-grants-2004_04
Patent number
US06720351B2

Reaction notes

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