Hydrazine hydrate (1:1) → Diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 4661Notes

Reaction equation

HRID 4661 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]([CH3:44])=[C:6]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH:7]([C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=2[O:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]2C(=O)C3=CC=CC=C3C2=O)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2].O.NN>C(O)C>[NH2:28][CH2:27][CH2:26][CH2:25][CH2:24][O:23][C:15]1[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:14]=1[CH:7]1[C:6]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[C:5]([CH3:44])[NH:4][C:3]([CH2:1][CH3:2])=[C:8]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20151538Diethyl 2-ethyl-4-[2-(4-phthalimidobutoxy)-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 14050495Diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylateYield 65.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 12.4 g of diethyl 2-ethyl-4-[2-(4-phthalimidobutoxy)-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate and 10.4 g of hydrazine monohydrate in 270 ml of 95% ethanol (water: 5%) was refluxed under heating for 10 hours. After cooling the reaction solution, the solution was concentrated under reduced pressure, and the residue was extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Crude crystals thus obtained were recrystallized from chloroform-ether to give 6.4 g of diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. temperatureunder heating for 10 hours
  2. temperatureAfter cooling the reaction solution
  3. concentrationthe solution was concentrated under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customCrude crystals thus obtained
  9. customwere recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-ae47bef14953469995ecbc681d8031ce
Source dataset
uspto-grants-1988_02
Patent number
US04727082

Reaction notes

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