HCID 8176949, compound → HCID 22993356, compound

HRID 1167615Notes

Reaction equation

HRID 1167615 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=[C:5]([N+:19]([O-])=O)[CH:4]=1>C(O)C.O1CCCC1.[Ni]>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[O:7][CH2:8][CH:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:19][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 8176949HCID 8176949, compound

Product 1

HCID 22993356HCID 22993356, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The compound obtained in Step A (3 g; 10.44 mmol) is dissolved in a Parr reactor with an ethanol/tetrahydrofuran mixture (1/1). Raney nickel (30% by weight, 900 mg) is then added. The mixture is left for 48 hours at 50° C. under a hydrogen pressure of 50 psi. After returning to ambient temperature, the solution is filtered over Celite and the filtrate is evaporated. The crude reaction product is purified by flash chromatography on silica gel (eluant: PE/AcOEt (85/15)). The title product is obtained in the form of a yellow solid.

Workup

  1. customAfter returning to ambient temperature
  2. filtrationthe solution is filtered over Celite
  3. customthe filtrate is evaporated
  4. customThe crude reaction product
  5. customis purified by flash chromatography on silica gel (eluant: PE/AcOEt (85/15))

Sources & evidence

ORD record
ord-3d6c9763ea214d25a9cd6f08dfe2a84b
Source dataset
uspto-grants-2003_09
Patent number
US06620809B2

Reaction notes

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