HCID 11391236, compound → HCID 3381362, compound

HRID 1685327Notes

Reaction equation

HRID 1685327 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][N+:11]([O-])=O)=[CH:5][CH:4]=1>CO.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][NH2:11])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 11391236HCID 11391236, compound

Product 1

HCID 3381362HCID 3381362, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To prewashed (3× water, 3×MeOH) RaNi (0.40 g) in MeOH (10 mL) was added 1-methoxy-4-(2-nitro-1-phenylethyl)benzene (0.188 g, 0.73 mmol), then shaken under H2 atmosphere (35 psi) in Parr shaker overnight. The reaction was filtered through Celite, washed with MeOH. The filtrate was concentrated to afford the product (155 mg, 94%) as a solid: 1H NMR (400 MHz, CDCl3) δ ppm 7.11-7.36 (7H, m), 6.79-6.89 (2H, m), 4.21 1H, (t, J=7.45 Hz), 3.76 (3H, s), 3.24 (2H, d, J=8.84 Hz).

Workup

  1. filtrationThe reaction was filtered through Celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a5db972579a0407b84917dddbb7e83c4
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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