Ethyl Acetate → HCID 22167067, compound

HRID 621593Notes

Reaction equation

HRID 621593 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:16]=2)=[CH:10][CH:9]=1.[C:26](OCC)(=[O:28])[CH3:27]>CCCCCC.O1CCCC1>[C:20]1([N:17]2[CH2:18][CH2:19][C:15]([N:14]([C:11]3[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=3)[C:26](=[O:28])[CH3:27])=[N:16]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 178418339ButyllithiumHCID 178492216HCID 178492216, compound

Product 1

HCID 22167067HCID 22167067, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

1.7M n-butyl lithium in hexane (7.0 ml) was added dropwise to a solution of 4,5-dihydro-N-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-amine (2.67 g) in tetrahydrofuran (150 ml) at -25° under N2. After 40 minutes ethyl acetate was added and the solution was allowed to reach room temperature. After being stirred for 2 hours, the solution was evaporated to dryness and the residue chromatographed on silica gel eluting with ethyl acetate in dichloromethane to give an oil which crystallised on trituration with ether. The solid was recrystallised from ether and hexane to give the title compound (0.82 g) mp 83°-5° (dec).

Workup

  1. customto reach room temperature
  2. customthe solution was evaporated to dryness
  3. customthe residue chromatographed on silica gel eluting with ethyl acetate in dichloromethane
  4. customto give an oil which
  5. customcrystallised on trituration with ether
  6. customThe solid was recrystallised from ether and hexane

Sources & evidence

ORD record
ord-4317bf4293de43cb93603eb4bd2f5e4d
Source dataset
uspto-grants-1989_04
Patent number
US04824859

Reaction notes

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