Acetic Acid → HCID 12621369, compound

HRID 1730163Notes

Reaction equation

HRID 1730163 reaction equation
[CH3:1][C:2]([N+:23]([O-])=O)([CH3:22])[CH:3]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)=O.[C:26](O)(=[O:28])[CH3:27].C(OC(=O)C)(=O)C>[Zn].N1C=CC=CC=1>[CH3:1][C:2]1([CH3:22])[N:23]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:26](=[O:28])[CH3:27])=[CH:9][CH:8]=2)[CH2:4][CH:3]1[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 126214264-Methyl-4-nitro-1-(4-nitrophenyl)-3-(pyridin-4-yl)pentan-1-one

Product 1

HCID 12621369HCID 12621369, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 1049PyridineSolvent

Procedure

18 G. of zinc powder are added to a solution of 18.0 g. of 4-methyl-4,4'-dinitro-3-(4-pyridyl)-valerophenone in 500 ml. of glacial acetic acid while stirring. After one hour, an additional 18 g. of zinc powder are added and the reaction mixture is left to react overnight. Then the reaction mixture is filtered, the filter residue is washed with dilute acetic acid and the filtrate evaporated under reduced pressure. The resulting residue is treated with dilute ammonia solution and extracted with ethyl acetate. The extract is dried over sodium sulfate and evaporated under reduced pressure to obtain a residue, which is then treated with a mixture of 70 ml. of acetic anhydride and 35 ml. of pyridine. After 1 hour, the crystals which precipitate are filtered off and washed with ethyl acetate to yield 4'-[5,5-dimethyl-4-(4-pyridyl)-1-pyrrolin-2-yl]-acetanilide, which is recrystallized from methanol to give a product with a melting point of 227°-228° C.

Workup

  1. waitthe reaction mixture is left
  2. customto react overnight
  3. filtrationThen the reaction mixture is filtered
  4. washthe filter residue is washed with dilute acetic acid
  5. customthe filtrate evaporated under reduced pressure
  6. additionThe resulting residue is treated with dilute ammonia solution
  7. extractionextracted with ethyl acetate
  8. dry with materialThe extract is dried over sodium sulfate
  9. customevaporated under reduced pressure
  10. customto obtain a residue, which
  11. additionis then treated with a mixture of 70 ml
  12. waitAfter 1 hour
  13. filtrationthe crystals which precipitate are filtered off
  14. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-2cc15551b7744810940b37fc3250c29f
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

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