Hydrochloric Acid → 2-Cyano-3-(1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl)-3-oxo-propanoic acid, ethyl ester

HRID 21543

Reaction equation

HRID 21543 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[H-].[Na+].[C:11]1([N:17]2[C:21]3[C:22]4[C:27]([CH2:28][C:20]=3[C:19]([C:29](Cl)=[O:30])=[N:18]2)=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>O1CCOCC1>[C:1]([CH:3]([C:29]([C:19]1[C:20]2[CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:18]=1)=[O:30])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 199325731,4-Dihydro-1-phenyl-indeno [1,2-c]pyrazole-3-carbonyl chloride

Product 1

HCID 867487242-Cyano-3-(1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl)-3-oxo-propanoic acid, ethyl esterYield 58.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Ethyl cyanoacetate (1.4 g) is treated with 50% sodium hydride (0.58 g) in anhydrous dioxane (20 ml) under stirring at room temperature until the effervescence subsides. To this solution 1,4-dihydro-1-phenyl-indeno [1,2-c]pyrazole-3-carbonyl chloride (3 g), prepared according to Example 5, dissolved in anhydrous dioxane (50 ml) is added under stirring at room temperature. The reaction mixture is allowed to react for 20 hours, then it is dilusted with ice water and acidified to pH 3 with 37% HCl. The precipitate is extracted with ethyl acetate and the organic solution washed with water and then evaporated to dryness in vacuo. The residue is purified over a SiO2 column, using hexane-ethyl acetate 80:20 as eluent, to give 2-cyano-3-(1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl) -3-oxo-propanoic acid, ethyl ester (2.2 g), which is reacted with aniline (3.4 g) in xylene (100 ml) at the reflux temperature for 48 hours. After cooling the precipitate is filtered and washed with xylene, then crystallized from dichloro-methane/methanol to give 1.2 g of 2-cyano-3-(1,4-dihydro-1-phenyl-indeno [1,2-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide, m.p. 273°-277° C.

Workup

  1. additionis added
  2. stirringunder stirring at room temperature
  3. customto react for 20 hours
  4. extractionThe precipitate is extracted with ethyl acetate
  5. washthe organic solution washed with water
  6. customevaporated to dryness in vacuo
  7. customThe residue is purified over a SiO2 column

Sources & evidence

ORD record
ord-0e89178175e34a6189d3666a06522396
Source dataset
uspto-grants-1995_06
Patent number
US05424308

Linked notes

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