Hydrochloric Acid → HCID 136347710, compound

HRID 1866457Notes

Reaction equation

HRID 1866457 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH2:24][C:25](=[O:34])[N:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:27]=3)=[CH:19][CH:18]=2)[CH:8]=[CH:9][C:10]=1[O:11]COC.Cl>CO>[OH:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH2:24][C:25](=[O:34])[N:26]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:27]=3)=[CH:21][CH:22]=2)[CH:8]=[CH:9][C:10]=1[OH:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68980107HCID 68980107, compound2×

Product 1

HCID 136347710HCID 136347710, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-{4-[2-(3,4-bis-methoxymethoxy-phenyl)-vinyl]-phenyl}-2-phenyl-2,4-dihydro-pyrazol-3-one (the cruce reaction product from Example 32) and conc. HCl in MeOH was stirred at room temperature for overnight. Evaporation of the solvent and purification by flash chromatography eluting with 10-15% MeOH in DCM, gave 5-{4-[2-(3,4-dihydroxy-phenyl)-vinyl]-phenyl}-2-phenyl-2,4-dihydro-pyrazol-3-one. 1H NMR (CD3OD+CDCl3, 300 MHz): 7.75-6.45(m, all aromatic peaks). 13C NMR (CD3OD+CDCl3, 75 MHz): 168.65, 148.27, 144.57, 144.36, 142.01, 132.16, 130.44, 129.07, 128.75, 126.94, 121.37, 120.82, 115.66, 115.08, 113.49. MS: 347 and 371 (MH+).

Workup

  1. customEvaporation of the solvent and purification by flash chromatography
  2. washeluting with 10-15% MeOH in DCM

Sources & evidence

ORD record
ord-f1622665c1db4dfd8e7382ba3e72a971
Source dataset
uspto-grants-2009_12
Patent number
US07629375B2

Reaction notes

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