Hydrazine hydrate (1:1) → HCID 13563418, compound

HRID 232697Notes

Reaction equation

HRID 232697 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:43])=[C:5]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:32]2C(=O)C3=CC=CC=C3C2=O)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].O.NN>C(O)C>[CH3:43][C:4]1[NH:3][C:2]([CH3:1])=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:5]=1[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH2:32])=[O:22]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13752662HCID 13752662, compound

Product 1

HCID 13563418HCID 13563418, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 16 g of methyl 8-phthalimidooctyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 6.8 g of hydrazine monohydrate in 160 ml of ethanol was refluxed for 2 hours under heating. Precipitates (solid) thus formed was removed by filtration. The filtrate was concentrated under reduced pressure and after adding chloroform to the residue, precipitates again removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography. The product was eluted with chloroform-methanol (8:2 v/v), and crude crystals were recrystallized from ethanol--petroleum ether to provide 6 g of 8-aminooctyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. temperatureunder heating
  2. customPrecipitates (solid)
  3. customthus formed
  4. customwas removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionafter adding chloroform to the residue
  7. customprecipitates again
  8. customremoved by filtration
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. washThe product was eluted with chloroform-methanol (8:2 v/v)
  11. customcrude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-4e6c77bc08974b3193a9309356a1f283
Source dataset
uspto-grants-1997_01
Patent number
US05591757

Reaction notes

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