Ethyl Acetate → HCID 10757270, compound

HRID 2292756Notes

Reaction equation

HRID 2292756 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:7]([CH3:19])=[C:6]2[CH2:20][C:21]([NH:23]N)=[O:22].CCOC(C)=O.CO.CCOC(C)=O>[Ni].CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:7]([CH3:19])=[C:6]2[CH2:20][C:21]([NH2:23])=[O:22]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10829831HCID 10829831, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 10757270HCID 10757270, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Using the procedure in Example 6, Part C, 200 mg (0.62 mmol) of 5-methoxy-2-methyl-1-[(2-pyridyl)methyl]-1H-indole-3-acetic acid hydrazide and approximately 1 gram of Raney nickel in 10 mL of EtOH were reacted to give after chromatographing twice on silica eluting with EtOAc followed by 5% MeOH/EtOAc, 54 mg (28% yield) of 5-methoxy-2-methyl-1-[(2-pyridyl)methyl]-1H-indole-3-acetamide, as a semi-solid material.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4d6936705f11488ca285739a966cd4d0
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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