HCID 22716445, compound → HCID 22716433, compound

HRID 1582878Notes

Reaction equation

HRID 1582878 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([O:19][CH3:20])[C:13]([O:21][CH3:22])=[CH:12]3)=[C:5]([N+:23]([O-])=O)[CH:4]=1>C(OCC)(=O)C.[Pd]>[NH2:23][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([O:19][CH3:20])[C:13]([O:21][CH3:22])=[CH:12]2

Participants

4

Reactant 1

HCID 22716445HCID 22716445, compound

Product 1

HCID 22716433HCID 22716433, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-(4-Methoxy-2-nitrophenyl)-2,3-dimethoxynaphthalene 29 (18 mg, 0.053 mmol) was hydrogenated overnight in ethyl acetate (20 mL) at 40˜45 lb./sq. in. using 10% palladium on carbon (10 mg) as catalyst. The reaction solution was passed through a Celite bed and the catalyst was washed with ethyl acetate (10 mL×3). Concentration in vacuo gave the crude product. The residue was chromatographed using a 60:40 mixture of hexanes:ethyl acetate to give 32 (14 mg) in 85% yield; 1H NMR (CDCl3) δ3.83 (3H, s), 4.01 (3H, s), 4.03 (3H, s), 6.37 (1H, d, J=2.5), 6.45 (1H, dd, J1=8.3, J2=2.4), 7.12-7.16 (3H, m), 7.42 (1H, dd, J1=8.4, J2=1.7), 7.72-7.77 (2H, m); 13C NMR δ55.72, 56.40, 101.56, 104.79, 106.59, 106.78, 121.49, 126.36, 126.81, 127.24, 128.47, 129.89, 131.98, 135.55, 145.28, 150.01, 150.25, 160.49; HRMS (EI) calcd for C19H19NO3 m/z: 309.1365; found: 309.1355.

Workup

  1. washthe catalyst was washed with ethyl acetate (10 mL×3)
  2. concentrationConcentration in vacuo
  3. customgave the crude product
  4. customThe residue was chromatographed
  5. additiona 60:40 mixture of hexanes

Sources & evidence

ORD record
ord-2dca4ba1f2984517ae81b43130083771
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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