(4-(Benzyloxy)phenyl)hydrazine monohydrochloride → 1-(4-Benzyloxyphenyl)-8-methoxy-3-methyl-4,5-dihydro-1H-benzo[g]indazole

HRID 598769Notes

Reaction equation

HRID 598769 reaction equation
[C:1]([CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[CH:9][CH:10]=2)[C:5]1=O)(=O)[CH3:2].Cl.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][NH2:33])=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C.O>[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]2[C:5]3[C:6]4[CH:7]=[C:8]([O:14][CH3:15])[CH:9]=[CH:10][C:11]=4[CH2:12][CH2:13][C:4]=3[C:1]([CH3:2])=[N:33]2)=[CH:30][CH:31]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochlorideHCID 190953982-Acetyl-7-methoxy-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 589487671-(4-Benzyloxyphenyl)-8-methoxy-3-methyl-4,5-dihydro-1H-benzo[g]indazoleYield 32.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Acetyl-7-methoxy-3,4-dihydro-2H-naphthalen-1-one (72.5 mg, 0.33 mmol) and 4-benzyloxyphenylhydrazine hydrochloride (90 mg, 0.36 mmol) were heated in ethanol at 70° C. for 2.5 days. The reaction was diluted with water and extracted with ethyl acetate. The organic extracts were washed with 1 N HCl, saturated sodium bicarbonate solution, and brine, dried over MgSO4, and concentrated. SiO2 chromatography with 5-20% ethyl acetate/hexanes gave 42 mg of the desired product. LC-MS (C26H24N2O2 calculated 396) m/z 397 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with 1 N HCl, saturated sodium bicarbonate solution, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-53c9d3b1802d425ca29fb5e81984c91c
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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