HCID 73703362, compound → HCID 20744324, compound

HRID 2307416Notes

Reaction equation

HRID 2307416 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]([O:16][CH3:17])=[O:15])[CH2:9][CH2:8]2)[CH3:4]>[Ni].CO.N.O>[OH-:1].[NH4+:2].[CH3:14][OH:15].[CH3:17][O:16][C:14]([N:10]1[C:11]2[C:7](=[CH:6][C:5]([CH:3]([NH2:2])[CH3:4])=[CH:13][CH:12]=2)[CH2:8][CH2:9]1)=[O:15]

Participants

5

Reactant 1

HCID 73703362HCID 73703362, compound

Product 2

HCID 20744324HCID 20744324, compoundYield 73%HCID 21894508Ammonium hydroxide methanolYield 30%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 140995658HCID 140995658, compoundSolvent

Procedure

A mixture of 2,3-dihydro-5-[1-(hydroxyimino)ethyl]-1H-indole-1-carboxylic acid, methyl ester, Preparation 19 (6 g, 25.6 mmol), and Raney nickel (1 mL) in methanol/ammonia/water (75 mL:15 mL) was hydrogenated (H2, 50 psi) for 3 days. The reaction mixture was filtered, and the resultant filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica eluting with a gradient system of solvents: ethyl acetate (100%) to ammonium hydroxide/methanol (30%) to provide the title compound (4.1 g, 73%) as a solid.

Workup

  1. customfor 3 days
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe resultant filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica eluting with a gradient system of solvents

Sources & evidence

ORD record
ord-2d6e5023a810426397a45aa9f4c63322
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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