Hydrazine → HCID 22022030, compound

HRID 897002Notes

Reaction equation

HRID 897002 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:23])[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:11]([CH3:14])[C:12]=1O.[NH2:24][NH2:25]>C(O)C>[CH3:22][O:21][C:17]1[CH:16]=[C:15]([C:10]2[C:9](=[O:23])[NH:24][N:25]=[C:12]([CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[C:11]=2[CH3:14])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22022100HCID 22022100, compound

Product 1

HCID 22022030HCID 22022030, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-fluorophenyl)-3-hydroxy-4-methyl-5-(3-methoxyphenyl)-2,4-cyclopentadienone (310 mg, 1 mmol) and hydrazine (0.2 mL) in ethanol (5 mL) was heated at reflux for 30 minutes. The resulting solution was concentrated in vacuo and the residue was dissolved in dichloromethane, dried over sodium sulfate, filtered and concentrated in vacuo to give the desired compound as a colorless oil. 1H NMR (CDCl3): 2.14 (s, 3H), 3.27 (d, J=13.8 Hz, 1H), 3.43 (d, J=13.8 Hz, 1H), 6.70-7.25 (m, 8H); MS: 325 (MH+).

Workup

  1. temperatureat reflux for 30 minutes
  2. concentrationThe resulting solution was concentrated in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48de91fa026a4492a67766b4bc2c17bb
Source dataset
uspto-grants-2005_07
Patent number
US06921761B2

Reaction notes

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