Formaldehyde → HCID 19852395, compound

HRID 1607220Notes

Reaction equation

HRID 1607220 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.O.[NH2:16][NH2:17].[CH2:18]=O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:18][NH:17][N:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 24654Hydrazine hydrate (1:1)HCID 735885Methyl (4-chlorobenzoyl)acetate

Product 1

HCID 19852395HCID 19852395, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 20.0 g of methyl 3-(4-chlorophenyl)-3-keto-propanoate in 100 ml of methanol was added a mixture of 4.7 g of hydrazine monohydrate and 7.6 g of 37% formalin in 50 ml of methanol. The reaction was stirred at room temperature for 18 hrs. The methanol was then removed in vacuo and the product was dissolved in 40 ml of methylene chloride and washed 5 times with 100 ml portions of water. The methylene chloride layer was dried over anhydrous magnesium sulfate and evaporated in vacuo to yield 22 g of 3-(4-chlorophenyl)-4-carbomethoxy-4,5-dihydro-1H-pyrazole which was used without further purification in the next reaction.

Workup

  1. customThe methanol was then removed in vacuo
  2. dissolutionthe product was dissolved in 40 ml of methylene chloride
  3. washwashed 5 times with 100 ml portions of water
  4. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-43133b0fe7d846a9bb980eac675b02f0
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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