1-(4-Benzyloxyphenyl)-8-methoxy-3-methyl-4,5-dihydro-1H-benzo[g]indazole → 4-(8-Methoxy-3-methyl-4,5-dihydrobenzo[g]indazol-1-yl)-phenol

HRID 1013028Notes

Reaction equation

HRID 1013028 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:22]4[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:21]=4[CH2:20][CH2:19][C:18]=3[C:17]([CH3:30])=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.O1CCCC1.[Pd]>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:21]2[CH2:20][CH2:19][C:18]3[C:17]([CH3:30])=[N:16][N:15]([C:12]4[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=4)[C:23]=3[C:22]=2[CH:24]=1

Participants

4

Reactant 1

HCID 589487671-(4-Benzyloxyphenyl)-8-methoxy-3-methyl-4,5-dihydro-1H-benzo[g]indazole

Product 1

HCID 589487654-(8-Methoxy-3-methyl-4,5-dihydrobenzo[g]indazol-1-yl)-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-(4-Benzyloxyphenyl)-8-methoxy-3-methyl-4,5-dihydro-1H-benzo[g]indazole (42 mg, 0.1 mmol) was dissolved in methanol/tetrahydrofuran (2/1, v/v, 1.5 mL) and a catalytic amount of 10% Pd/C (wet) was added. The flask was purged with nitrogen and hydrogen, then stirred under 1 atmosphere of hydrogen for 2 hours. The mixture was filtered through Celite and washed with methanol, and the filtrate was concentrated. The reaction was assumed to be quantitative. LC-MS (C19H18N2O2 calculated 306) m/z 307 (M+H).

Workup

  1. customThe flask was purged with nitrogen and hydrogen
  2. filtrationThe mixture was filtered through Celite
  3. washwashed with methanol
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bc830927bc09406888e285f17aca42e1
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

Loading…