2-Ethylpyridine → HCID 70562833, compound

HRID 1974104Notes

Reaction equation

HRID 1974104 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH2:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)C.[C:20](OC(=O)C)(=O)C>>[CH3:20][C:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])=[CH:12][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 3

HCID 75232-EthylpyridineHCID 7918Acetic AnhydrideHCID 111012-Nitrobenzaldehyde

Product 1

HCID 70562833HCID 70562833, compound

Procedure

A mixture of o-nitrobenzaldehyde (127 g., 0.84 mole), 2-ethylpyridine (90 g., 0.84 mole) and acetic anhydride (171 g., 1.68 mole) is heated at reflux for 24 hr. Excess acetic anhydride is evaporated in vacuo and the residue poured into 500 ml. of water. The mixture is adjusted to pH 11 with 50% NaOH providing a precipitate which is collected and dried. Crystallization from isopropyl ether yields 136.7 g. (67%) of 2(-β-methyl-2-nitrostyryl)-pyridine, m.p. 62° -64° C. which, after a second crystallization, is analytically pure.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 hr
  3. customExcess acetic anhydride is evaporated in vacuo
  4. additionthe residue poured into 500 ml
  5. customis collected
  6. customdried
  7. customCrystallization from isopropyl ether
  8. customyields 136.7 g
  9. custom(67%) of 2(-β-methyl-2-nitrostyryl)-pyridine, m.p. 62° -64° C. which, after a second crystallization

Sources & evidence

ORD record
ord-57ef42d79fcc4b73b5414af80c0dcb5d
Source dataset
uspto-grants-1976_12
Patent number
US04000143

Reaction notes

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