Ethyl Acetoacetate → HCID 796646, compound

HRID 1904945Notes

Reaction equation

HRID 1904945 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](OCC)(=[O:14])[CH2:10][C:11]([CH3:13])=O.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[OH:8][C:7]1[C:2]2=[N:1][C:11]([CH3:13])=[CH:10][C:9](=[O:14])[N:3]2[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 796646HCID 796646, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 1.1 g of 2-amino-3-hydroxypyridine VIII and 1.1 g of etyl acetoacetate is added 4 ml of polyphosphoric acid and the resultant mixture is stirred under heating at 100° C. for 4 hours. The reaction mixture is poured into ice water, and the resulting solution is adjusted to PH 4 with 2N aqueous sodium hydroxide, then to PH 7 with aqueous sodium carbonate and shaken with CHCl3. The organic layer is washed with water and dried over anhydrous sodium sulfate. The solvent is evaporated to give 0.9 g of the titled compound XV-1.

Workup

  1. washThe organic layer is washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent is evaporated

Sources & evidence

ORD record
ord-a7c78a404bad44cb9a131f3edb4ecd53
Source dataset
uspto-grants-1989_06
Patent number
US04840953

Reaction notes

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