Ethyl Acetate → HCID 13121197, compound

HRID 371418Notes

Reaction equation

HRID 371418 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:21])=[C:5]([C:18]([O-])=O)[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.O>[C:12]1([CH:6]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:2]([CH3:1])[NH:3][C:4]([CH3:21])=[C:5]2[CH3:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 20130298HCID 20130298, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13121197HCID 13121197, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

24.1 g (80 millimols) of methyl 1,4-dihydro-2,6-dimethyl-4-phenyl-pyridine-3,5-dicarboxylate were introduced in portions, at 60° C. and while stirring, into a solution of 12.2 g (320 millimols) of LiAlH4 in 400 ml of absolute tetrahydrofuran (N2 atmosphere), and the mixture was stirred for a further 6 to 7 hours at 60° C. After the mixture had cooled, 19.7 ml of ethyl acetate, 15.9 ml of water, 19.6 ml of 10N NaOH and 15.9 ml of water were successively added dropwise. The mixture was then filtered under suction, the residue was rinsed thoroughly with ether, and the filtrate was evaporated down in vacuo. The syrupy residue was dissolved in 50 ml of ether, and the solution was left in a cold place to crystallize giving 7.4 g of the above compound (36% of theory). After recrystallization from acetonitrile, colorless prisms; melting point 120° C., were obtained.

Workup

  1. temperatureAfter the mixture had cooled
  2. filtrationThe mixture was then filtered under suction
  3. washthe residue was rinsed thoroughly with ether
  4. customthe filtrate was evaporated down in vacuo
  5. dissolutionThe syrupy residue was dissolved in 50 ml of ether
  6. waitthe solution was left in a cold place
  7. customto crystallize

Sources & evidence

ORD record
ord-182ecb9e0dbd4fe69a7553596f1c12d3
Source dataset
uspto-grants-1985_07
Patent number
US04532248

Reaction notes

Loading…