Hydrazine hydrate (1:1) → HCID 178515607, compound

HRID 644823Notes

Reaction equation

HRID 644823 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]([CH2:11][C:12](OC)=[O:13])=O)=[CH:7][CH:6]=1>C(O)C>[Cl:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]2[NH:3][N:2]=[C:12]([OH:13])[CH:11]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

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

Product 1

HCID 178515607HCID 178515607, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (0.80 g, 20 mmol) was added to a solution of methyl 4-chlorobenzoylacetate (3.19 g, 15.0 mmol) in ethanol (40 ml) at 0° C., and the mixture was stirred at room temperature for 2 days. After completion of the reaction, a precipitated solid was filtered and washed with diethyl ether, to give a white solid of 5-(4-chlorophenyl)-3-hydroxypyrazole (2.02 g, yield: 55.1%). mp: 240-241° C.; 1H-NMR (DMSO-d6, DMSO, ppm): δ 5.92 (s, 1H), 7.47 (d, J=8.5 Hz, 2H), 7.70 (d, J=8.5 Hz, 2H), 9.30-10.60 (br s, 1H), 11.60-12.70 (br s, 1H).

Workup

  1. customAfter completion of the reaction
  2. filtrationa precipitated solid was filtered
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a55eda3facd74354b3efe18365d9f6d7
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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