HCID 22716441, compound → HCID 22716431, compound

HRID 1582880Notes

Reaction equation

HRID 1582880 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:23]([O-])=O)=[C:7]([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)[CH:8]=1>C(OCC)(=O)C.[Pd]>[NH2:23][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=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 22716441HCID 22716441, compound

Product 1

HCID 22716431HCID 22716431, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Crude 6-(5-methoxy-2-nitrophenyl)-2,3-dimethoxynaphthalene 30 (100 mg, approximately 90% pure) was hydrogenated overnight in ethyl acetate (40 mL) at 40˜45 lb./sq. in. using 10% palladium on carbon (30 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 50:50 mixture of hexanes:ethyl acetate to give 33 (66 mg); mp 158-160° C.; IR (KBr) 3408, 3354, 2936, 1633, 1499, 1249, 1166 cm−1; 1H NMR (CDCl3) δ3.57 (2H, s), 3.79 (3H, s), 4.01 (3H, s), 4.03 (3H, s), 6.77-6.84 (3H, m), 7.15 (1H, s), 7.16 (1H, s), 7.45 (1H, dd, J1=8.3, J2=1.8), 7.75-7.79 (2H, m); 13C NMR δ56.34, 56.42, 106.59, 106.85, 114.80, 116.35, 117.41, 125.99, 126.81, 127.32, 128.73, 129.42, 129.82, 135.75, 137.89, 150.19, 150.32, 153.25; HRMS (EI) calcd for C19H19NO3 m/z: 309.1365; found: 309.1375.

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 50:50 mixture of hexanes

Sources & evidence

ORD record
ord-385248aed8fa437f9fbf8f94204a9485
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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