HCID 12621362, compound → HCID 12621404, compound

HRID 1730153Notes

Reaction equation

HRID 1730153 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=O)[CH2:14][CH:15]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[C:16]([CH3:21])([N+:18]([O-])=O)[CH3:17])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]>[Zn].C(O)(=O)C>[CH3:17][C:16]1([CH3:21])[C@@H:15]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH2:14][C@H:13]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[NH:18]1

Participants

4

Reactant 1

HCID 12621362HCID 12621362, compound

Product 1

HCID 12621404HCID 12621404, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

A solution of 34 g. of 3',4',5'-trimethoxy-4-methyl-4-nitro-3-(4-pyridyl)-valerophenone in 340 ml. of glacial acetic acid is heated at 50°-60° C. with stirring. There are added portionwise 34 g. of zinc dust. The resulting mixture is left to react for 1 hour. Then a further 34 g. of zinc dust are added and after another hour, the reaction mixture is filtered. The filter residue is washed with glacial acetic acid and the filtrate evaporated under reduced pressure. The residue is taken up in water, make alkaline with potassium carbonate and extracted three times with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue which results is crystallized with ether to obtain trans-4-[2,2-dimethyl-5-(3,4,5-trimethoxyphenyl)-3-pyrrolidinyl]-pyridine with a melting point of 117°-119° C. The corresponding oxalate, recrystallized from methanol, has a melting point of 228°-230° C. (decomp.).

Workup

  1. additionThere are added portionwise 34 g
  2. waitThe resulting mixture is left
  3. customto react for 1 hour
  4. filtrationthe reaction mixture is filtered
  5. washThe filter residue is washed with glacial acetic acid
  6. customthe filtrate evaporated under reduced pressure
  7. extractionextracted three times with ethyl acetate
  8. washThe organic phase is washed with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated under reduced pressure
  11. customThe residue which results
  12. customis crystallized with ether

Sources & evidence

ORD record
ord-d14507d71cda47f28302048d5bab755a
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

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