Hydrazine → HCID 12200544, compound

HRID 246331Notes

Reaction equation

HRID 246331 reaction equation
O/[CH:2]=[C:3]1\[C:4](=O)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]\1.[NH2:11][NH2:12]>CO>[NH:11]1[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:3]=2[CH:2]=[N:12]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 21779761HCID 21779761, compound

Product 1

HCID 12200544HCID 12200544, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[1-hydroxy-meth-(Z)-ylidene]-cycloheptanone (1.35 g, 9.63 mmol) in MeOH (10 mL) at 0° C. was added hydrazine (0.30 mL, 9.63 mmol) dropwise. The yellow reaction mixture was stirred at room temperature for 30 min then concentrated. The residue was dissolved in CH2Cl2 and washed with water. The organic layer was dried over MgSO4 and concentrated to provide 1.24 g (95%) of 1,4,5,6,7,8-hexahydrocycloheptapyrazole as a pale yellow solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 7.28 (s, 1H), 2.75-2.82 (m, 2H), 2.54-2.62 (m, 2H), 1.80-1.91 (m, 2H), 1.60-1.75 (m, 4H).

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-02bb673992024ed0880b4475dc8f4205
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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