HCID 22339808, compound → HCID 69419608, compound

HRID 916172Notes

Reaction equation

HRID 916172 reaction equation
[C:1]([NH:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]CC3C=CC([N+]([O-])=O)=CC=3)=[C:12]([O:27][CH3:28])[CH:11]=2)S[C:6]=1[C:29]([O:31][CH3:32])=[O:30])(=[O:3])[CH3:2]>[Ni].CCOC(C)=O>[CH3:32][O:31][C:29](=[O:30])[CH2:6][CH:5]([CH2:9][CH2:8][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:27][CH3:28])[CH:11]=1)[NH:4][C:1](=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 22339808HCID 22339808, compound

Product 1

HCID 69419608HCID 69419608, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-acetamido-5-[3-methoxy-4-(4-nitrobenzyloxy) phenyl]thiophene-2-carboxylate (1.4481 g, 3.17 mmol) was reductively desulfurized using Raney nickel. The filtered solution was taken up in hot EtOAc then washed with 0.5 N HCl (2×30 mL) and H2O. The organic layer was dried (MgSO4), filtered and concentrated to yield the title compound as a yellow oil (0.5620 g, 1.90 mmol, 60.0%); TLC: Rf=0.80 (Solvent L); IR (cm−1): 3498 (OH), 2905 (CH aliphatic), 1743 (ester C═O), 1663 (amide C═O), 726 (═CH); 1H nmr (CDCl3): δ 6.82 (., 1H, J=7.9 Hz), 6.67 (m, 2H), 6.10 (br d, 1H, J=8.6 Hz), 5.56 (br s, 1H), 4.28 (m, 1H), 3.88 (s, 3H), 3.68 (s, 3H), 2.60 (d, 2H, J=8.4 Hz), 2.55 (t, 2H, J=2.2 Hz), 1.97 (s, 3H), 1.85 (m, 2H).

Workup

  1. washthen washed with 0.5 N HCl (2×30 mL) and H2O
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dbfaa57e43c040bb8c23743086e225d7
Source dataset
uspto-grants-2007_09
Patent number
US07268164B2

Reaction notes

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