HCID 54262640, compound → HCID 5477084, compound

HRID 1730646Notes

Reaction equation

HRID 1730646 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[CH:9][C:10](OCC)=[O:11])=[C:6]([CH3:15])[C:5]([NH:16]C(=O)C)=[C:4]([CH3:20])[N:3]=1>Cl>[NH2:16][C:5]1[C:6]([CH3:15])=[C:7]2[C:2](=[N:3][C:4]=1[CH3:20])[NH:1][C:10](=[O:11])[CH:9]=[CH:8]2

Participants

3

Reactant 1

HCID 54262640HCID 54262640, compound

Product 1

HCID 5477084HCID 5477084, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ethyl 3-(2-amino-5-acetamido-4,6-dimethylpyrid-3-yl)-acrylate (2.48 g., 8.95 mmole) is heated under reflux in solution in 6N hydrochloric acid (24.8 ml.) for 6 days. The reaction mixture is filtered through a glass-fiber filter disc, the filtrate diluted slowly over a period of 15 minutes with ethanol (75 ml.) whereupon 1.043 g. (51.7%) of product in the form of the hydrochloride crystallizes from solution, m.p. 325° C. (dec.). A second crop raises the yield to 79%. Following recrystallization of the crude product from a mixture of dilute hydrochloric acid and isopropanol the purified product melts at 325° C. (dec.).

Workup

  1. filtrationThe reaction mixture is filtered through a glass-fiber
  2. filtrationfilter disc
  3. additionthe filtrate diluted slowly over a period of 15 minutes with ethanol (75 ml.) whereupon 1.043 g
  4. custom(51.7%) of product in the form of the hydrochloride crystallizes from solution, m.p. 325° C. (dec.)
  5. temperatureA second crop raises the
  6. customyield to 79%
  7. customrecrystallization of the crude product
  8. additionfrom a mixture of dilute hydrochloric acid and isopropanol the purified product melts at 325° C. (dec.)

Sources & evidence

ORD record
ord-3c84bc1cd5604314b660256c0c92ecc8
Source dataset
uspto-grants-1976_11
Patent number
US03993656

Reaction notes

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