Isopropanol → HCID 9951255, compound

HRID 2303388Notes

Reaction equation

HRID 2303388 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:30])[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)[CH:12]=2)=[O:10])=[CH:3][CH:2]=1.C(O)(C)C.[H][H]>[Ni].O1CCOCC1>[N:1]1[CH:2]=[CH:3][C:4]([NH:7][C:8](=[O:30])[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=3)[CH:12]=2)=[O:10])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 15521669HCID 15521669, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9951255HCID 9951255, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 200 mg of Raney nickel in 50 ml of dioxane is treated with a suspension of 320 mg (0.8 mmol) of N-(pyridin-4-yl)-[1-(4-nitrobenzyl)indol-3-yl]glyoxyl-amide in a solvent mixture of 150 ml of dioxane and 20 ml of isopropanol. Hydrogen is passed into this suspension with shaking at a gas pressure of 5 bar and the temperature is kept at 30-35° C. After about 3 hours, a further 400 mg of Raney nickel are added and the hydrogenation is continued at 35° C. and 5 bar for a further 8 hours with vigorous shaking. The catalyst is filtered off under an N2 atmosphere, the filtrate is concentrated to dryness in vacuo and the residue is dried in vacuo at 40° C.

Workup

  1. customis kept at 30-35° C
  2. customis continued at 35° C.
  3. wait5 bar for a further 8 hours with vigorous shaking
  4. filtrationThe catalyst is filtered off under an N2 atmosphere
  5. concentrationthe filtrate is concentrated to dryness in vacuo
  6. customthe residue is dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-6f826ca5eec44eb6aff900a0f7ed8138
Source dataset
uspto-grants-2002_08
Patent number
US06432987B1

Reaction notes

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