HCID 18999061, compound → HCID 18999058, compound

HRID 2260799Notes

Reaction equation

HRID 2260799 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([C:12]1[CH:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)=[O:11])([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([C:12]1[CH:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)=[O:11]

Participants

4

Reactant 1

HCID 18999061HCID 18999061, compound

Product 1

HCID 18999058HCID 18999058, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (1 g) was added to a solution of (2-nitrophenyl)-(6-methoxypyridin-3-yl)methanone (3.6 g) in ethanol (100 ml) and the mixture was hydrogenated at 10 psi (0.7×105N.m-2) for 30 minutes. The reaction mixture was filtered then evaporated to dryness. The residue was purified by column chromatography on silica using ethyl acetate/petroleum ether (60-80) (1:4) to afford the title compound as a yellow solid (2.78 g). mp 60°-62° C. Rf =0.50 in 33% ethyl acetate/petroleum ether (60-80) on silica plates; 1H NMR (360 MHz, CDCl3) δ 4.01 (3H, s), 6.64 (1H, ddd, J=1.5 and 8 Hz), 6.74 (1H, d, J=8 Hz), 6.81 (1H, d, J=9 Hz), 7.29 (1H, ddd, J=1.5 and 8 Hz), 7.46 (1H, dd, J=1.5 and 8 Hz), 7.93 (1H, dd, J=3 and 9 Hz), 8.48 (1H, d, J=3 Hz); MS, m/z 228 for M+ ; IR (KBr) 1620 and 1600 cm-1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthen evaporated to dryness
  3. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-98cfacc88d13433b80ea30c39b86ce72
Source dataset
uspto-grants-1995_12
Patent number
US05478933

Reaction notes

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