HCID 59200437, compound → HCID 59200445, compound

HRID 1685315Notes

Reaction equation

HRID 1685315 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][N+:14]([O-])=O>[Ni].CO>[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][NH2:14]

Participants

4

Reactant 1

HCID 59200437HCID 59200437, compound

Product 1

HCID 59200445HCID 59200445, compoundYield 122.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel (3.4 g) was placed in Parr flask and was washed with MeOH (3×), then 1-((methoxymethoxy)methyl)-2-(2-nitro-1-phenylethyl)benzene (2.93 g, 9.72 mmol) in MeOH (150 mL) was added. The flask was installed on a Parr shaker, purged first with argon (3×) then H2 (3×) then pressurized to ˜35 psi and shaken over a weekend. The reaction was depressurized, then was filtered and concentrated to give 3.22 g of an oil. The residue was dissolved in CHCl3, dried (MgSO4), filtered through Celite and concentrated to afford the product (2.57 g) as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 7.35 (s, 4H), 7.13-7.31 (m, 5H), 4.70 (d, J=11.87 Hz, 3H), 4.66 (s, 3H), 4.51 (d, J=11.62 Hz, 2H), 4.35 (t, J=6.06 Hz, 1H), 3.39 (s, 3H).

Workup

  1. washwas washed with MeOH (3×)
  2. custompurged first with argon (3×)
  3. filtrationwas filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2a5c87736cb540c88387dbbdf01eae4e
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

Loading…