HCID 73703363, compound → HCID 20744332, compound

HRID 2307409Notes

Reaction equation

HRID 2307409 reaction equation
O[N:2]=[C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:12]2)=[CH:7][CH:6]=1)[CH3:4]>[Ni].CO.[OH-].[NH4+]>[CH3:18][O:17][C:15]([N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][C:5]([CH:3]([NH2:2])[CH3:4])=[CH:6][CH:7]=2)[CH2:12]1)=[O:16]

Participants

5

Reactant 1

HCID 73703363HCID 73703363, compound

Product 1

HCID 20744332HCID 20744332, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A suspension of 1,2,3,4-tetrahydro-7-[1-(hydroxyimino)ethyl]-isoquinoline-2-carboxylic acid, methyl ester, Preparation 9 (9.9 g, 40 mmol) and Raney nickel (1 mL) in methanol (50 mL) and ammonium hydroxide (15 mL) was hydrogenated (H2, 50 psi) for 3 days. The reaction mixture was then filtered and the resultant filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica using a gradient system of solvents: ethyl acetate (100%) to ammonium hydroxide/methanol (30%). The product was obtained as an oil (6.55 g, 70%).

Workup

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

Sources & evidence

ORD record
ord-87836ee65d074688937e52f3caf4371d
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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