HCID 59431290, compound → Ethyl 2-(4-amino-2-methyl-1H-indol-1-yl)acetate

HRID 505931Notes

Reaction equation

HRID 505931 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[C:7]([CH3:19])[N:8]2[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])([O-])=O.[H][H]>C(OCC)(=O)C.[Pt]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[C:7]([CH3:19])[N:8]2[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 59431290HCID 59431290, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59431293Ethyl 2-(4-amino-2-methyl-1H-indol-1-yl)acetate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (4-nitro-2-methyl-1H-indol-1-yl)-acetic acid, ethyl ester (5.0 g, 19 mmol) in ethyl acetate (75 ml) was hydrogenated under 3 bar hydrogen pressure in the presence of a wet 1% Pt/C catalyst paste (38 w/w, 0.7 g) until hydrogen uptake ceased (3 hours). The reaction mixture was filtered through kieselguhr and the solids washed with ethyl acetate (75 ml). The filtrate and wash were combined with solutions obtained from 2 previous experiments which had been carried out in a similar maimer, each on a 2 g scale, and evaporated to dryness to provide (4-amino-2-methyl-1H-indol-1-yl)-acetic acid, ethyl ester, 8.59 g, >100% as a brown oil which solidified on standing.

Workup

  1. custom(3 hours)
  2. filtrationThe reaction mixture was filtered through kieselguhr
  3. washthe solids washed with ethyl acetate (75 ml)
  4. washThe filtrate and wash
  5. customobtained from 2 previous experiments which
  6. customeach on a 2 g scale, and evaporated to dryness

Sources & evidence

ORD record
ord-7c1c62114e324e27bb98ebf169cc8eee
Source dataset
uspto-grants-2010_08
Patent number
US07781598B2

Reaction notes

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