4-Methoxyphenylhydrazine hydrochloride → HCID 67196072, compound

HRID 598765Notes

Reaction equation

HRID 598765 reaction equation
[C:1]([CH:4]1[CH2:13][CH2:12][CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[C:5]1=O)(=O)[CH3:2].Cl.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][NH2:25])=[CH:20][CH:19]=1>C(O)C.O>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:1]([CH3:2])=[C:4]3[C:5]([CH:6]4[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]4[CH2:12][CH2:13]3)=[N:25]2)=[CH:20][CH:19]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:5]3[CH:6]4[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]4[CH2:12][CH2:13][C:4]=3[C:1]([CH3:2])=[N:25]2)=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 67197066HCID 67197066, compound

Product 2

HCID 67196072HCID 67196072, compoundHCID 67197076HCID 67197076, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

2-Acetyloctahydronaphthalen-1-one (0.96 g, 4.95 mmol) was dissolved in absolute ethanol (10 mL), and 4-methoxyphenylhydrazine hydrochloride (0.95 g, 5.44 mmol) was added. The reaction was stirred overnight at 70° C. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with 1 N HCl, saturated sodium bicarbonate solution, and brine, then dried over MgSO4 and concentrated. SiO2 chromatography with 5-40% ethyl acetate/hexanes gave 0.15 g of 2-(4-methoxyphenyl)-3-methyl-4,5,5a,6,7,8,9,9a-octahydro-2H-benzo[g]indazole and 0.66 g of 1-(4-methoxyphenyl)-3-methyl-4,5,5a,6,7,8,9,9a-octahydro-1H-benzo[g]indazole. Regiochemistry was determined by x-ray crystal structure of 1-(4-methoxyphenyl)-3-methyl-4,5,5a,6,7,8,9,9a-octahydro-1H-benzo[g]indazole. LC-MS (C19H24N2O calculated 296) m/z 297 (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-2b0e29c7d2374f0bb2c383b6fdc74e23
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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