HCID 18717653, compound → HCID 70012865, compound

HRID 840560Notes

Reaction equation

HRID 840560 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[C:16]([N+:22]([O-])=O)[CH:17]=[C:18]([Cl:21])[CH:19]=2)[NH:14][C:13](=[O:25])[C@@H:12]1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Ni]>[NH2:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[C:20]2[C:15]=1[NH:14][C:13](=[O:25])[C@H:12]([CH3:26])[N:11]2[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

5

Reactant 2

HCID 18717653HCID 18717653, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 70012865HCID 70012865, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

The compound of Example IV (1.5 g, 4.0 mmol) was dissolved in 150 ml of methanol and hydrogenated at room temperature with Raney nickel catalysis, using 1 atm hydrogen. When the calculated amount of hydrogen had been taken up, the catalyst was removed by filtration with suction, and the filtrate was concentrated in vacuo. The product was purified by silica gel chromatography using ethyl acetate/heptane=2:1 as eluent. The yield was 0.68 g (49%) of brownish solid of melting point 152-154° C.

Workup

  1. customthe catalyst was removed by filtration with suction
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e618fa1dac554939894f2818a9f8dd3d
Source dataset
uspto-grants-2002_04
Patent number
US06369057B1

Reaction notes

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