Ammonium Chloride → 4-(3-Fluoro-4-methylphenyl)-1-trimethylacetyl-1,4-dihydropyridine

HRID 1032714

Reaction equation

HRID 1032714 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[F:8][C:9]1[CH:14]=[C:13](Cl)[CH:12]=[CH:11][C:10]=1[CH3:16].[Mg].[Cl-].[NH4+:19]>O1CCCC1.N1C=CC=CC=1>[F:8][C:9]1[CH:14]=[C:13]([CH:9]2[CH:14]=[CH:13][N:19]([C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])[CH:11]=[CH:10]2)[CH:12]=[CH:11][C:10]=1[CH3:16]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 5206304-Chloro-2-fluorotolueneHCID 5462224Magnesium

Product 1

HCID 148519734-(3-Fluoro-4-methylphenyl)-1-trimethylacetyl-1,4-dihydropyridine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a solution of 45 ml pyridine in 800 ml tetrahydrofuran (THF) was added dropwise 50 ml trimethylacetyl chloride. The mixture was stirred 3 hrs. at room temperature, 4.0 g cuprous iodide was added, and the mixture stirred for 1 hr. longer. The mixture was then cooled to -40° C. and a Grignard reagent prepared from 45 ml 2-fluoro-4-chlorotoluene and 10 g magnesium in 300 ml THF was added dropwise The reaction mixture was stirred overnight at room temperature, ammonium chloride solution added, and the product was extracted and isolated to give 90 g of an oil used directly in the next reaction.

Workup

  1. stirringthe mixture stirred for 1 hr
  2. additionwas added dropwise The reaction mixture
  3. stirringwas stirred overnight at room temperature
  4. extractionthe product was extracted
  5. customisolated

Sources & evidence

ORD record
ord-597cc87d81364b66a4448ffc9aee34c3
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Linked notes

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