Hydrazine hydrate (1:1) → HCID 23359386, compound

HRID 1195141Notes

Reaction equation

HRID 1195141 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:40])=[C:5]([C:21]([O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][N:29]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>[CH3:40][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][O:26][CH2:27][CH2:28][NH2:29])=[O:22]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23359375HCID 23359375, compound

Product 1

HCID 23359386HCID 23359386, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 9.14 g of methyl 2-(2-phthalimidoethoxy)ethyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 4,2 g of hydrazine monohydrate in 100 ml of ethanol was refluxed for 2 hours under heating. After cooling the reaction solution with ice and then adding thereto 100 ml of chloroform, precipitates were 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 4.8 g of 2-(2-aminoethoxy)ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate was obtained as liquid.

Workup

  1. temperatureunder heating
  2. temperatureAfter cooling the reaction solution with ice
  3. additionadding
  4. custom100 ml of chloroform, precipitates
  5. customwere removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. washThe product was eluted with chloroform-methanol (8:2 v/v)

Sources & evidence

ORD record
ord-0fcea184f1404ed193150d873b7e03fa
Source dataset
uspto-grants-1992_05
Patent number
US05110820

Reaction notes

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