2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → HCID 178474058, compound

HRID 276847Notes

Reaction equation

HRID 276847 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][N:6]=1)(=[O:3])[CH3:2].C([O:14][C:15](=O)[C:16](=[CH:19]OCC)[C:17]#[N:18])C>C1(C)C=CC=CC=1>[C:1]([NH:4][C:5]1[N:6]=[C:7]2[C:8](=[CH:9][CH:10]=1)[N:11]=[CH:19][C:16]([C:17]#[N:18])=[C:15]2[OH:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 27352192-Acetamido-5-aminopyridine

Product 1

HCID 178474058HCID 178474058, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
257.5 °C

Procedure

A solution of 2-acetamido-5-aminopyridine (1.6 g, 10.7 mmol) and ethyl(ethoxymethylene)cyanoacetate (3.6 g, 21.3 mmol) in toluene (50 ml) was heated at reflux for 10 hrs under argon. After cooling, the white solid was collected and dried. A solution of this solid in Dowtherm (250 ml) was heated at 255-260° C. for 6 hrs under nitrogen. During this process, ethanol was distilled off. The mixture was heated at 260° C. for an additional 5 hrs. After cooling, the mixture was poured in hexane. The solid was collected, dissolved in a 1:1 mixture of DMF and ethyl acetate, and ether was added to give the title compound as a solid. mass spectrum (electrospray, m/e): 228.7 (M+H); IR cm-1: 2228, 1682.; H-NMR δ(DMSO-d6): 2.182 (3H, s, CH3), 7.96 (1H, s, OH), 8.09 (1H, d, C7-H), 8.49 (1H, d, C8-H), 8.71 (1H, s, C2-H), 11.20 (1H, s, NH).

Workup

  1. temperatureat reflux for 10 hrs under argon
  2. temperatureAfter cooling
  3. customthe white solid was collected
  4. customdried
  5. distillationDuring this process, ethanol was distilled off
  6. temperatureThe mixture was heated at 260° C. for an additional 5 hrs
  7. temperatureAfter cooling
  8. additionthe mixture was poured in hexane
  9. customThe solid was collected
  10. dissolutiondissolved in a 1:1 mixture of DMF and ethyl acetate, and ether
  11. additionwas added

Sources & evidence

ORD record
ord-d685cde945694244b0cdbf51c3ac6867
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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