HCID 9888691, compound → HCID 135744186, compound

HRID 1582882Notes

Reaction equation

HRID 1582882 reaction equation
C([O:8][C:9]1[C:30]([O:31][CH3:32])=[CH:29][C:12]2[N:13]=[N:14][C:15]3[C:20]([C:11]=2[CH:10]=1)=[CH:19][CH:18]=[C:17]1[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][CH3:26])=[CH:24][C:16]=31)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[C:30]([O:31][CH3:32])=[CH:29][C:12]2[N:13]=[N:14][C:15]3[C:20]([C:11]=2[CH:10]=1)=[CH:19][CH:18]=[C:17]1[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][CH3:26])=[CH:24][C:16]=31

Participants

4

Reactant 1

HCID 9888691HCID 9888691, compound

Product 1

HCID 135744186HCID 135744186, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

9-Benzyloxy-2,3,8-trimethoxydibenzo[c,h]cinnoline, 42, (5 mg, 0.012 mmol) was hydrogenated overnight in ethyl acetate (25 mL) at 26 lb./sq. in. using 10% palladium on carbon (1.5 mg). The solution was passed through a Celite bed and the catalyst was washed with ethyl acetate (10 mL×3). Concentration of the ethyl acetate solution in vacuo gave the crude product. Chromatography using a 50:45:5 mixture of hexanes:ethyl acetate:methanol as eluting solvent gave compound 34 (3 mg) in 76% yield; 1H NMR (DMSO-d6) δ4.00 (3H, s), 4.10 (3H, s), 4.12 (3H, s), 7.66 (1H, s), 8.02 (2H, s), 8.21 (1H, d, J=8.4), 8.38 (1H, d, J=8.9), 8.96 (1H, s); 13C NMR δ55.9, 56.4, 103.1, 103.8, 108.5, 109.1, 117.4, 117.8, 118.0, 125.7, 128.1, 131.3, 140.4, 143.8, 150.5, 150.7, 151.3, 152.4; HRMS (EI) calcd for C19H16N2O4 m/z 336.111; found: 336.1109.

Workup

  1. washthe catalyst was washed with ethyl acetate (10 mL×3)
  2. customConcentration of the ethyl acetate solution in vacuo gave the crude product
  3. washethyl acetate:methanol as eluting solvent

Sources & evidence

ORD record
ord-e0e6a4834d2642ad97928e24d6e55c3d
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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