Water → 6,7-Dihydro-2H-benzo[6,7]cyclohepta[cd]indazol-5-ylmethanol

HRID 132991Notes

Reaction equation

HRID 132991 reaction equation
C([O:4][CH2:5][C:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[C:20](I)[C:12]=3[C:11](=O)[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=O)C.C(OCC1C2CCC3C=CC=CC=3C(=O)C=2C(I)=CC=1)(=O)C.O.O.[NH2:47][NH2:48]>N1C=CC=CC=1.CO>[N:47]1[NH:48][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][OH:4])=[C:16]3[CH2:15][CH2:14][C:13]4[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=4[C:11]=1[C:10]=23

Participants

7

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 12150903(6-iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetateHCID 12150904(4-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

Product 1

HCID 101252656,7-Dihydro-2H-benzo[6,7]cyclohepta[cd]indazol-5-ylmethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

2.1 g of the mixture of (6-iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate and (4-iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate prepared in Example 1-g was dissolved in a mixed solvent of 5 ml of pyridine and 5 ml of methanol, and 5 ml of hydrazine monohydrate was added, followed by heating under reflux for 3 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=3:7), to give 330 mg and 130 mg of the title compounds as a colorless powder, respectively.

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureunder reflux for 3 days
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified
  9. customseparated by silica gel column chromatography (ethyl acetate:hexane=3:7)

Sources & evidence

ORD record
ord-48f86f51cfc04367b2b7860a723c13d6
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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