Hydrazine → HCID 68980107, compound

HRID 1866456Notes

Reaction equation

HRID 1866456 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][O:24][CH3:25])=[C:18]([O:26][CH2:27][O:28][CH3:29])[CH:17]=2)=[CH:10][CH:9]=1)=O)C.[NH2:31][NH2:32]>CCO>[CH3:29][O:28][CH2:27][O:26][C:18]1[CH:17]=[C:16]([CH:15]=[CH:14][C:11]2[CH:10]=[CH:9][C:8]([C:6]3[CH2:5][C:4](=[O:3])[N:31]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:32]=3)=[CH:13][CH:12]=2)[CH:21]=[CH:20][C:19]=1[O:22][CH2:23][O:24][CH3:25]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 68979090HCID 68979090, compound

Product 1

HCID 68980107HCID 68980107, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-{4-[2-(3,4-bis-methoxymethoxy-phenyl)-vinyl]-phenyl}-3-oxo-propionic acid ethyl ester (400 mg) and hydrazine (excess) in EtOH (30 mL) was stirred at 90° C. for 5 hours. Evaporation and purification by flash chromatography eluted with 5-10% MeOH in DCM gave 5-{4-[2-(3,4-bis-methoxymethoxy-phenyl)-vinyl]-phenyl}-2-phenyl-2,4-dihydro-pyrazol-3-one as a yellow oil (260 mg). 1H NMR (CDCl3, 300 MHz): 7.95 (d, J=8.7 Hz, 2H), 7.62 (d, J=8.7 Hz, 2H), 7.40-7.00(m, 7H), 6.90 (d, 1H), 6.58 (d, J=12.0 Hz, 1H), 6.50 (d, J=12.0 Hz, 1H) 5.21, 5.07(2s, 4H, MOM), 3.78(s, 2H), 33.51, 3.41 (2s, 6H, MOM) ppm. 13C NMR (CDCl3, 75 MHz 170.65, 154.82, 147.23, 147.15, 140.38, 138.53, 131.56, 129.84, 129.68, 129.29, 128.88, 126.17, 125.69, 123.72, 119.42, 117.83, 116.67, 56.69, 56.52, 40.03 ppm. MS: 459 (MH+).

Workup

  1. customEvaporation and purification by flash chromatography
  2. washeluted with 5-10% MeOH in DCM

Sources & evidence

ORD record
ord-023b3e4c32864a0195a271710d4ae318
Source dataset
uspto-grants-2009_12
Patent number
US07629375B2

Reaction notes

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