tert-Butyl 6-nitro-1H-indole-1-carboxylate → tert-Butyl 6-amino-2,3-dihydro-1H-indole-1-carboxylate

HRID 13511Notes

Reaction equation

HRID 13511 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 22240526tert-Butyl 6-nitro-1H-indole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 21936857tert-Butyl 6-amino-2,3-dihydro-1H-indole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

6-Nitro-indole-1-carboxylic acid t-butyl ester (1 eq) was dissolved in methanol (0.1M), to this solution was added palladium on carbon (0.1 eq) in methanol under nitrogen. A hydrogen atmosphere was then inserted and resulting mixture allowed to stir for 3 hours at room temperature. The reaction mixture was then filtered through celite and solvent removed in vacuo to afford 6-Amino-2,3-dihydro-indole-1-carboxylic acid t-butyl ester as a white solid. MS: MH+ 235

Workup

  1. customresulting mixture
  2. filtrationThe reaction mixture was then filtered through celite and solvent
  3. customremoved in vacuo

Sources & evidence

ORD record
ord-9d61da34b45c47dba6c04990afa93756
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

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