Ethyl 2-methylacetoacetate → HCID 18918850, compound

HRID 1291203Notes

Reaction equation

HRID 1291203 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][CH:10]([C:16]([CH3:18])=O)[C:11](OCC)=[O:12].[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[OH:8][C:7]1[C:2]2=[N:1][C:16]([CH3:18])=[C:10]([CH3:9])[C:11](=[O:12])[N:3]2[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 701Ethyl 2-methylacetoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 18918850HCID 18918850, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-3-hydroxypyridine (11 g), ethyl 2-methylacetoacetate (14.4 g), polyphosphoric acid (20 ml), and acetic acid (40 ml) was heated at 100° C. with stirring for 4 hours. The reaction mixture was poured in ice-water, adjusted to pH 4 with aqueous sodium hydroxide solution and then to pH 7 with potassium carbonate. The resulting precipitate was extracted with chloroform and the extract was washed with water, dried, and concentrated to provide the title compound (3.63 g) as brown solid. 1H-NMR (DMSO-d6) δ: 2.25(3H,s), 2.49(3H,s), 6.97(1H,dd,J=7.4,6.8Hz), 7.05(1H,dd,J=7.4,1.6Hz), 8.47(1H,dd,J=6.8,1.6Hz).

Workup

  1. extractionThe resulting precipitate was extracted with chloroform
  2. washthe extract was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a1f3a6f72f1c4046b2af2f8531836aa6
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…