Hydrazine hydrate (1:1) → 5-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}-3-pyrazolone

HRID 1589148Notes

Reaction equation

HRID 1589148 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][C:22](=O)[CH2:23][C:24]([O:26]CC)=O)=[C:9]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].O.[NH2:36][NH2:37]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][C:22]2[N:37]=[N:36][C:24](=[O:26])[CH:23]=2)=[C:9]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70044209Ethyl 4-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetoacetate

Product 1

HCID 202481365-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}-3-pyrazoloneYield 38.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 4-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetoacetate (0.50 g) and hydrazine hydrate (0.50 g) in ethanol (20 ml) was kept at room temperature for 4 days and then evaporated. The residue was purified by chromatography on silica gel (1.0 g) using dichloromethane plus 0-5% by volume of methanol as eluant. Appropriate fractions were combined and evaporated and the residue crystallised from ethyl acetate to give the title compound (0.18 g), m.p. 207° C. Found: C,57.11; H,5.15; N,9.19. C22H24ClN3O6 requires: C,57.20; H,5.24; N,9.10%.

Workup

  1. customevaporated
  2. customThe residue was purified by chromatography on silica gel (1.0 g)
  3. customevaporated
  4. customthe residue crystallised from ethyl acetate

Sources & evidence

ORD record
ord-a50ddc7333e64d9d8dbf893a25f4030f
Source dataset
uspto-grants-1986_02
Patent number
US04568677

Reaction notes

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