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

HRID 968671Notes

Reaction equation

HRID 968671 reaction equation
[NH2:1][C:2]1[NH:3][N:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][C:8]=2[F:21])[CH2:5][CH:6]=1>C(Cl)Cl.O=[Mn]=O>[NH2:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][C:8]=2[F:21])[N:3]=1

Participants

4

Reactant 1

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

Product 1

HCID 115364983-Amino-1-(4-benzyloxy-2-fluorophenyl)-pyrazoleYield 27.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

MnO2 (2.66 g) was added to a solution of 3-amino-1-(4-benzyloxy-2-fluorophenyl) pyrazoline (3.86 g) in CH2Cl2 (40 mL), and the mixture was stirred at room temperature for 4 hours. The precipitate (MnO2) was filtered off, and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (EtOAc/hexane 1/9, 1/4, 1/2 and 1/1) and crystallization from EtOAc/hexane to yield 1.04 g of the title compound.

Workup

  1. filtrationThe precipitate (MnO2) was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography on silica gel (EtOAc/hexane 1/9, 1/4, 1/2 and 1/1) and crystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-61422f6c95984f6383c7c3ec71ffd108
Source dataset
uspto-grants-2007_12
Patent number
US07304072B2

Reaction notes

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