Styrene → 1-(3-Chlorophenyl)-1,4,5,6-tetrahydro-6-phenyl-3-pyridazinecarboxylic acid, ethyl ester

HRID 1768941Notes

Reaction equation

HRID 1768941 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl.[Cl:8][C:9]1[CH:10]=[C:11]([NH:15][NH2:16])[CH:12]=[CH:13][CH:14]=1.Br[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].[CH2:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[Cl:8][C:9]1[CH:10]=[C:11]([N:15]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][CH2:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:16]2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 7501StyreneHCID 10340Sodium CarbonateHCID 66144Ethyl bromopyruvateHCID 75331m-Chlorophenylhydrazine hydrochloride

Product 1

HCID 867483741-(3-Chlorophenyl)-1,4,5,6-tetrahydro-6-phenyl-3-pyridazinecarboxylic acid, ethyl esterYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 12.0 g (0.112 mol) of sodium carbonate suspended in 50 mL THF was added 5.0 g (0.028 mol) 3-chlorophenyl hydrazine hydrochloride, 6.5 g (0.033 mol) ethyl bromopyruvate and 44.0 g (0.42 mol) styrene. The reaction mixture was stirred at room temperature for 18 h, filtered through a plug of celite, rinsed with methylene chloride and concentrated under reduced pressure. The crude reaction mixture was flash chromatographed using 10% EtOAc/90% hexanes as eluent to afford 3.2 g of a yellow solid, mp 125-126° C. 1H NMR (CDCl3) δ: 1.39 (t, 3H), 1.8-2.3 (m, 3H), 2.7 (d, 1H), 4.35 (m, 2H), 5.12 (bs, 1H), 6.95 (m, 1H), 7.0-7.4 (m, 8H).

Workup

  1. filtrationfiltered through a plug of celite
  2. washrinsed with methylene chloride
  3. concentrationconcentrated under reduced pressure
  4. customThe crude reaction mixture
  5. customchromatographed

Sources & evidence

ORD record
ord-3dcb3a8279d44989b9ec3a14e6634a8a
Source dataset
uspto-grants-1995_01
Patent number
US05380718

Reaction notes

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