Acrylonitrile → 3-Amino-1-(4-benzyloxy-2-fluorophenyl) pyrazoline

HRID 968670Notes

Reaction equation

HRID 968670 reaction equation
C[O-].[Na+].[C:4](#[N:7])[CH:5]=[CH2:6].Cl.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[C:19]([F:25])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO.CCOC(C)=O>[NH2:7][C:4]1[NH:24][N:23]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:18][C:19]=2[F:25])[CH2:6][CH:5]=1

Participants

6

Reactant 3

HCID 7855Acrylonitrile2×HCID 10942334Sodium Methoxide2×HCID 116375674-Benzyloxy-2-fluorophenylhydrazine hydrochloride

Product 1

HCID 691586273-Amino-1-(4-benzyloxy-2-fluorophenyl) pyrazoline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaOMe (25 wt. % solution in MeOH, 7.75 mL) and acrylonitrile (2.1 mL) were added to a solution of 4-benzyloxy-2-fluorophenylhydrazine hydrochloride (4.15 g) in MeOH (40 mL) at room temperature. The mixture was stirred at room temperature for 30 minutes and refluxed overnight. Additional NaOMe (25 wt. % solution in MeOH, 3.9 mL) and acrylonitrile (1.05 ml) were added to the reaction mixture and refluxed for 7.5 hours. The mixture was diluted with EtOAc and washed with sat. NaHCO3 and brine. The organic layer was dried over anhydrous MgSO4 and concentrated. The residue was crystallized from CHCl3/hexane to yield 3.86 g of the title compound. NaOMe and MeOH means sodium methoxide and methanol, respectively.

Workup

  1. temperaturerefluxed overnight
  2. temperaturerefluxed for 7.5 hours
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was crystallized from CHCl3/hexane

Sources & evidence

ORD record
ord-843f1bab94fa4deeb927a63c1eb1c27e
Source dataset
uspto-grants-2007_12
Patent number
US07304072B2

Reaction notes

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