Hydrazine hydrate (1:1) → Ethyl 3-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-1H-pyrazole-5-carboxylate

HRID 880373Notes

Reaction equation

HRID 880373 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1[C:33](=O)[CH2:34][C:35](=O)[C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:44][NH2:45]>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=2)[C:10]=1[C:33]1[CH:34]=[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[NH:45][N:44]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66758581Ethyl 4-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-2,4-dioxobutanoate

Product 1

HCID 66759191Ethyl 3-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-1H-pyrazole-5-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of ethyl 4-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-2,4-dioxobutanoate (1 g, 1.75 mmol) and hydrazine hydrate (0.25 mL, 4.4 mmol) in ethanol (20 mL) was refluxed for 1 hour. The formed precipitate was filtered off and washed with ethanol and dried, to afford the title compound (0.69 g, 70% yield).

Workup

  1. filtrationThe formed precipitate was filtered off
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-b51dfa31d0d944799572576295027b9d
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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