Dichloromethane → Opc 15161

HRID 2255168Notes

Reaction equation

HRID 2255168 reaction equation
C([O:8][C:9]1[C:10]([CH2:28][CH:29]([CH3:31])[CH3:30])=[N+:11]([O-:27])[C:12]([O:25][CH3:26])=[C:13]([CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[N:14]=1)C1C=CC=CC=1.[H][H].ClCCl>CO.[C].[Pd]>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([CH2:15][C:13]2[NH:14][C:9](=[O:8])[C:10]([CH2:28][CH:29]([CH3:31])[CH3:30])=[N+:11]([O-:27])[C:12]=2[O:25][CH3:26])=[CH:17]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 15065179HCID 15065179, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 129359Opc 15161Yield 92%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In 140 ml of methanol was dissolved 2.69 g of 3-benzyloxy-5-(indol-3-yl)methyl-2-isobutyl-6-methoxypyrazine 1-oxide, thereto was added 10% palladium-carbon, and the mixture was stirred for 1 hour at room temperature in a hydrogen gas atmosphere. 150 Milliliters of dichloromethane was added, and the mixture was stirred for 20 minutes, then the catalyst was removed by filtration, and the filtrate was subjected to recrystallization from methanol-chloroform to obtain 1.94 g of the title compound as pale yellow prism-like crystals having a melting point of 222°-224° C.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe filtrate was subjected to recrystallization from methanol-chloroform

Sources & evidence

ORD record
ord-bb39987db9794093a461c8f3115a230a
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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