Hexane → Ethyl 2-cyano-3-(5-n-butyl-2-pyridylamino)acrylate

HRID 1701403Notes

Reaction equation

HRID 1701403 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][N:3]=1.C(O[CH:15]=[C:16]([C:22]#[N:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])C.CCCCCC>C1(C)C=CC=CC=1>[C:22]([C:16](=[CH:15][NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][N:3]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:23]

Participants

5

Reactant 3

HCID 8058HexaneHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 184286505-Butylpyridin-2-amine

Product 1

HCID 70514903Ethyl 2-cyano-3-(5-n-butyl-2-pyridylamino)acrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-amino-5-n-butylpyridine (3.72 g., 23.43 mmoles) and ethyl ethoxymethylenecyanoacetate (3.96 g., 23.43 mmoles) in toluene was heated for 10 minutes by means of an oil bath maintained at 100°. The solution was cooled and treated with Skellysolve B (200 ml.). The mixture was triturated for 18 hours at room temperature and then filtered. The collected title compound (4.3 g., 67.2%) had m.p. 69°-73°.

Workup

  1. temperaturemaintained at 100°
  2. temperatureThe solution was cooled
  3. customThe mixture was triturated for 18 hours at room temperature
  4. filtrationfiltered
  5. customThe collected title compound (4.3 g., 67.2%)

Sources & evidence

ORD record
ord-bef42e2dcac442f4a4680cca8b943415
Source dataset
uspto-grants-1980_03
Patent number
US04192944

Reaction notes

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