Hydrazine hydrate (1:1) → Dimethyl 4-[2-(4-aminobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 4659Notes

Reaction equation

HRID 4659 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:12]=2[CH:21]2[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([CH3:31])[NH:24][C:23]([CH3:32])=[C:22]2[C:33]([O:35][CH3:36])=[O:34])C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:18])=[O:19])=[CH:13][C:12]=1[CH:21]1[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([CH3:31])[NH:24][C:23]([CH3:32])=[C:22]1[C:33]([O:35][CH3:36])=[O:34]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20151519Dimethyl 4-[2-(4-phthalimidobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 14050493Dimethyl 4-[2-(4-aminobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 48.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.9 g of dimethyl 4-[2-(4-phthalimidobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 5.9 g of hydrazine monohydrate in 170 ml of % ethanol(water: 5%) was refluxed under heating for 6 hours. After cooling, the reaction solution was concentrated under reduced pressure. The residue was extracted with chloroform, and 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 2.6 g of dimethyl 4-[2-(4-aminobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. temperatureunder heating for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction 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-3665349bb73843b2bd458f0e58887d4d
Source dataset
uspto-grants-1988_02
Patent number
US04727082

Reaction notes

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