Ethyl 2-chloroacetoacetate → Ethyl 8-amino-6-(aminocarbonyl)-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 427506Notes

Reaction equation

HRID 427506 reaction equation
[NH2:1][C:2]1[C:3]([NH2:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].[CH2:12]([O:14][C:15](=[O:21])[CH:16](Cl)[C:17]([CH3:19])=O)[CH3:13]>C(O)C>[NH2:1][C:2]1[C:3]2[N:4]([C:16]([C:15]([O:14][CH2:12][CH3:13])=[O:21])=[C:17]([CH3:19])[N:11]=2)[CH:5]=[C:6]([C:7]([NH2:9])=[O:8])[CH:10]=1

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 99421905,6-Diaminonicotinamide

Product 1

HCID 18357447Ethyl 8-amino-6-(aminocarbonyl)-2-methylimidazo[1,2-a]pyridine-3-carboxylateYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5,6-Diaminonicotinamide (2.0 g, 13.4 mmol), ethyl-2-chloroacetoacetate (2.38 g, 14.4 mmol) and ethanol (40 ml) were refluxed for 20 h. The precipitate was isolated by filtration and washed with ethanol and diethyl ether. The solids were suspended in water, basified with a sodium hydroxide solution and isolated by filtration. Washing the solids with water and diethyl ether gave 0.42 g (12%) of the desired product.

Workup

  1. customThe precipitate was isolated by filtration
  2. washwashed with ethanol and diethyl ether
  3. customisolated by filtration
  4. washWashing the solids with water and diethyl ether

Sources & evidence

ORD record
ord-2b22776d263345f19074e980817f6d80
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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