3-Aminopropionitrile → Ethyl 7-chloro-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1696935Notes

Reaction equation

HRID 1696935 reaction equation
Cl[C:2]1[C:7]([C:8](/[C:10](=[CH:16]/[N:17]([CH3:19])C)/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:20])[N:3]=1.[NH2:21][CH2:22][CH2:23]C#N>C(O)C.C(OCC)C>[Cl:20][C:4]1[N:3]=[C:2]2[C:7]([C:8](=[O:9])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][N:17]2[CH2:19][CH2:23][C:22]#[N:21])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 16473-AminopropionitrileHCID 15675736Ethyl (2Z)-2-((2,6-dichloropyridin-3-yl)carbonyl)-3-(dimethylamino)prop-2-enoate

Product 1

HCID 87333475Ethyl 7-chloro-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 21585056Diethyl ether ethanolSolvent

Conditions

Temperature
75 °C

Procedure

A solution of EXAMPLE 81A (20 g) and 3-aminopropionitrile (4.9 mL) in 1:1 ethanol/diethyl ether (400 mL) was stirred for 15 minutes, diluted with hexanes (1 L), and filtered. The filtrant was dissolved in acetonitrile (400 mL), and the resulting solution was treated with potassium carbonate (17.4 g), heated at 75° C. for 18 hours then cooled, diluted with water (1.5 L), stirred for 1 hour, and filtered.

Workup

  1. filtrationfiltered
  2. dissolutionThe filtrant was dissolved in acetonitrile (400 mL)
  3. additionthe resulting solution was treated with potassium carbonate (17.4 g)
  4. temperaturethen cooled
  5. additiondiluted with water (1.5 L)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2d11fef41e544d75b34d55a10652b3f1
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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