Hydrazine hydrate (1:1) → HCID 13752660, compound

HRID 232696Notes

Reaction equation

HRID 232696 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:42])=[C:5]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]2C(=O)C3=CC=CC=C3C2=O)=[O:23])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].O.NN>C(O)C>[CH3:42][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]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[C:5]=1[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH2:31])=[O:23]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13752659HCID 13752659, compound

Product 1

HCID 13752660HCID 13752660, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 11.2 g of methyl 6-phthalimidohexyl 2,6-dimethyl-4-(m-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 10.1 g of hydrazine monohydrate in 330 ml of 95% ethanol (containing water of 5%) was refluxed for 4 hours under heating. After cooling the reaction solution, the 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. Crude crystal were recrystallized from chloroform-ether to provide 2.6 g of 6-aminohexyl methyl 2,6-dimethyl-4-(m-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. temperatureunder heating
  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
  8. customCrude crystal were recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-d6b48ef441d04b32af9e9f2298d1a30b
Source dataset
uspto-grants-1997_01
Patent number
US05591757

Reaction notes

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