Ammonium Hydroxide → DIMETHYL 1,4-DIHYDRO-2,6-DIISOPROPYL-4-(4-FLUOROPHENYL)-PYRIDINE-3,5-DICARBOXYLATE

HRID 1709655Notes

Reaction equation

HRID 1709655 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5](=O)[CH:6]([CH3:8])[CH3:7].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[OH-:20].[NH4+:21]>CO>[C:3]([C:4]1[CH:16]([C:15]2[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=2)[C:4]([C:3]([O:2][CH3:1])=[O:20])=[C:5]([CH:6]([CH3:8])[CH3:7])[NH:21][C:5]=1[CH:6]([CH3:8])[CH3:7])([O:2][CH3:1])=[O:10]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 680234-FluorobenzaldehydeHCID 2759969Methyl 4-methyl-3-oxopentanoate

Product 1

HCID 11199700DIMETHYL 1,4-DIHYDRO-2,6-DIISOPROPYL-4-(4-FLUOROPHENYL)-PYRIDINE-3,5-DICARBOXYLATE

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 152 g (1.05 mole) 4-methyl-3-oxopentanic acid methyl ester, 56 ml (1.05 mole) 4-fluoro benzaldehyde and 40 ml conc. ammonium hydroxide was heated to reflux in 200 ml methanol for 48 hours. The reaction mixture was then concentrated in vacuo, the viscous residue was dissolved in 500 ml ethylether and washed with saturated sodium bisulfite. The organic layer was dried over magnesium sulfate, filtered and evaporated to yield 202 g of the Step 1 title product. Analysis for C21H26FNO4. calc; C, 67.18; H, 6.98; N, 3,73. Found: C, 67.40; H, 7.48; N, 3.88.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. dissolutionthe viscous residue was dissolved in 500 ml ethylether
  4. washwashed with saturated sodium bisulfite
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6604b154d7244ec88f154bba03a606ed
Source dataset
uspto-grants-1990_08
Patent number
US04950675

Reaction notes

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