Hydrazine hydrate (1:1) → HCID 178469913, compound

HRID 251928Notes

Reaction equation

HRID 251928 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6](=[CH:12][N:13](C)C)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=O.O.[NH2:21]N>C(O)(=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12][NH:13][N:21]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54509863Ethyl 2-(2-chlorobenzoyl)-3-dimethylaminopropenoate

Product 1

HCID 178469913HCID 178469913, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.41 g of ethyl 2-(2-chlorobenzoyl)-3-(N,N-dimethylamino)acrylate (a compound described in JP-A 7-101940), 0.30 g of hydrazine monohydrate and 5 ml of acetic acid was stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure. Water was poured into the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain ethyl 3-(2-chlorophenyl)-1H-pyrazole-4-carboxylate of the formula:

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was poured into the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e3da5b4612a46aeb04f4340b64e7861
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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