2-Nitropropane → HCID 12621362, compound

HRID 1730155Notes

Reaction equation

HRID 1730155 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:22])[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[N+:23]([CH:26]([CH3:28])[CH3:27])([O-:25])=[O:24].C(O)C.CC[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:22])[CH2:14][CH:15]([C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)[C:26]([CH3:28])([N+:23]([O-:25])=[O:24])[CH3:27])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 3982-NitropropaneHCID 702EthanolHCID 2723922Sodium ethoxideHCID 540288583-(Pyridin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Product 1

HCID 12621362HCID 12621362, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 40 g. of 3',4',5'-trimethoxy-3-(4-pyridyl)-acrylophenone and 24 g. of 2-nitropropane in 270 ml. of ethanol is heated at reflux with stirring under a nitrogen atmosphere. Within 1 hour there is added dropwise a sodium ethylate solution (manufactured from 1.35 g. of sodium and 27 ml. of ethanol). The reaction mixture left standing for a half hour to react further is then evaporated under reduced pressure. The residue results is taken up in methylene chloride, washed with water, dried over sodium sulfate and evaporated under reduced pressure. The product which results is crystallized with chloroform ether to yield 3',4',5'-trimethoxy-4-methyl-4-nitro-3-(4-pyridyl)-valerophenone, melting point 214°-216° C.

Workup

  1. temperatureat reflux
  2. waitThe reaction mixture left
  3. waitstanding for a half hour
  4. customto react further
  5. customis then evaporated under reduced pressure
  6. customThe residue results
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated under reduced pressure
  10. customThe product which results
  11. customis crystallized with chloroform ether

Sources & evidence

ORD record
ord-86da33ee5be4429697b5679ec2ee1fd7
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

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