(4-Benzyloxy-phenyl)-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone → (4-Hydroxy-phenyl)-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone

HRID 220914Notes

Reaction equation

HRID 220914 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:26][C:25]3[CH:24]=[N:23][N:22]([CH3:27])[C:21]=3[NH:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:26][C:25]3[CH:24]=[N:23][N:22]([CH3:27])[C:21]=3[NH:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 136128429(4-Benzyloxy-phenyl)-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone

Product 1

HCID 136128422(4-Hydroxy-phenyl)-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanoneYield 22%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(4-Benzyloxy-phenyl)-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone from Example E75.1 (800 mg, 1.95 mmol) was dissolved in methanol (100 ml) and hydrogenated over 10% Pd/C catalyst (400 mg) for 7 h. The mixture was filtered through Celite® filter agent, washed with chloroform and methanol and the filtrate was concentrated in vacuo to yield the title compound (140 mg, 22%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. filtrationfilter agent
  3. washwashed with chloroform and methanol
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-84b804dddd124c9981d7c22aa49435f3
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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