HCID 18798661, compound → HCID 18736891, compound

HRID 356535Notes

Reaction equation

HRID 356535 reaction equation
[CH3:1][CH:2]([C:4](=[O:16])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:3].[H][H]>[Ni].C1COCC1>[NH2:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][C:4](=[O:16])[CH:2]([CH3:1])[CH3:3])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 18798661HCID 18798661, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18736891HCID 18736891, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 13.6 g (62 mmol) of 2-methyl-5-(4-nitro-phenyl)-pentan-3-one (Y. Huang, L. Shi, S. Li, Synthesis, 1988, 975-977), 400 mL of THF, and 2.6 g of Raney Nickel was shaken in a hydrogen atmosphere (24 p.s.i.) at 25° C. for 56 hours. The catalyst was filtered, and the filtrate was concentrated to give the title compound. 1H NMR (CDCl3) δ 1.01 (d, 6 H), 2.46-2.55 (m, 1 H), 2.65-2.83 (m, 4 H), 3.55 (br s, 2 H), 6.56 (d, 2 H), 6.92 (d, 2 H).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1977f739d7d74c809f3c7b0994b6b33d
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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