Triethylamine → Ethyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-B][1,4]oxazine-2-carboxylate

HRID 493312

Reaction equation

HRID 493312 reaction equation
Cl[CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5]CC)=O.[OH:13][C:14]1[C:15]([NH2:20])=[N:16][CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>CCO>[CH2:11]([O:10][C:8]([CH:2]1[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[N:16][C:15]=2[NH:20][C:3]1=[O:5])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 281142-Amino-3-HydroxypyridineHCID 84182Diethyl chloromalonate

Product 1

HCID 12079662Ethyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-B][1,4]oxazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl chloromalonate (9.73 g, 50 mmol) was added to a stirred mixture of 3-hydroxy-2-aminopyridine (5.51 g, 50 mmol), triethylamine (6.97 mL, 50 mmol) and EtOH (100 mL) at room temperature. The mixture was heated at reflux for 17 h and allowed to attain room temperature. The precipitate formed was filtered off, washed with EtOH and dried to give the product as a white solid: yield 3.85 g (35%); mp 160-162° C. Anal. (C10H10N2O4) C, H, N.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 17 h
  3. customto attain room temperature
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with EtOH
  7. customdried

Sources & evidence

ORD record
ord-467614d302e848cabad7e4708b5a6bc4
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Linked notes

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