Dichloromethane → HCID 178434273, compound

HRID 343111Notes

Reaction equation

HRID 343111 reaction equation
F[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][NH2:12].C(Cl)Cl>C(O)CO>[CH3:2][C:3]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:12][N:11]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 99472-Fluoro-1-phenylethan-1-one

Product 1

HCID 178434273HCID 178434273, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a stirring solution of 36.2 g (0.26 mol) of 2-Fluoroacetophenone in 120 mL of ethylene glycol is added 8.6 mL (0.27 mol, 1.05 equiv.) of hydrazine. The resulting solution is stirred 2 h at RT and then heated at 165° C. for 40 h. The solution is cooled to RT, poured into CH2Cl2 (200 mL) and extracted with H2O (2×200 mL). The organic layers were combined, dried (MgSO4), and the solvent removed in vacuo. Purification of the crude material by recrystallization form hexane/CHCl3 afforded 26 g of 3-Methylindazole as a light tan solid: 1H NMR (CDCl3, 300 MHz) δ7.73 (d, 1H, J=8.1), 7.44 (m, 2H), 7.19 (dd, 1H, J=7.0,7.0), 2.67 (s, 3H).

Workup

  1. temperatureheated at 165° C. for 40 h
  2. temperatureThe solution is cooled to RT
  3. extractionextracted with H2O (2×200 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customPurification of the crude material
  7. customby recrystallization
  8. customform hexane/CHCl3

Sources & evidence

ORD record
ord-dfdfc85cc09543fb94334c97c6e5ea90
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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