HCID 22716423, compound → HCID 22716427, compound

HRID 1582870Notes

Reaction equation

HRID 1582870 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([O:20][CH3:21])[C:14]([O:22][CH3:23])=[CH:13]2)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([O:20][CH3:21])[C:14]([O:22][CH3:23])=[CH:13]2

Participants

4

Reactant 1

HCID 22716423HCID 22716423, compound

Product 1

HCID 22716427HCID 22716427, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-(2-Nitrophenyl)-2,3-dimethoxynaphthalene (70 mg, 0.23 mmol) was hydrogenated overnight in ethyl acetate (45 mL) at 40-45 lb./sq. in. under catalysis of palladium (10 wt % on activated carbon, 20 mg). The solution was passeded through a celite bed and the catalyst was washed with ethyl acetate (3×10 mL). Concentration in vacuo gave compound 5 (60 mg) in 99% yield; 1H NMR (CDCl3) d 4.02(3H, s), 4.04(3H, s), 6.82(1H, d, J=8.0), 6.85˜6.93 (1H, m), 7.16(1H, s), 7.18(1H, s), 7.20˜7.26(2H m), 7.47(1H, dd, J=8.3, J=1.6), 7.78(1H, d, J=8.8), 7.80(1H, s); 13C NMR d 56.4, 106.6, 106.9, 116.1, 119.2, 126.1, 126.8, 127.3, 128.3, 128.7, 128.9, 129.9, 131.2, 135.8, 144.3, 150.2, 150.3.

Workup

  1. washthe catalyst was washed with ethyl acetate (3×10 mL)
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-ef73c72cbd7846d592e69c92cd4716cc
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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