2-Amino-3-Hydroxypyridine → HCID 10016099, compound

HRID 640810Notes

Reaction equation

HRID 640810 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O:11][C:12](=O)[CH:13]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH:14]=O)C>CCO>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[C:12](=[O:11])[N:3]3[CH:4]=[CH:5][CH:6]=[C:7]([OH:8])[C:2]3=[N:1][CH:14]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 281142-Amino-3-HydroxypyridineHCID 13174739HCID 13174739, compound

Product 1

HCID 10016099HCID 10016099, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-3-hydroxypyridine (5.51 g, 0.05 mol) and 2-(4-chlorophenyl)-3-oxo-propanoic acid ethyl ester (13.6 g, 0.06 mol) in EtOH (100 mL) were heated under reflux for 15 h and then allowed to cool. The precipitate was isolated via filtration to yield a 9:1 mixture of the enamine and the cyclized product (11.1 g).

Workup

  1. temperatureunder reflux for 15 h
  2. temperatureto cool
  3. customThe precipitate was isolated via filtration
  4. customto yield

Sources & evidence

ORD record
ord-5ecc852d2ddd48dabdbf612e14a3905d
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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