Diethyl (ethoxymethylene)malonate → Diethyl 6-ethoxy-3-pyridylaminomethylenemalonate

HRID 479855

Reaction equation

HRID 479855 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][N:5]=1)[CH3:2].C(O[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:6][N:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 30403016-Ethoxypyridin-3-amine

Product 1

HCID 621746Diethyl 6-ethoxy-3-pyridylaminomethylenemalonateYield 93.7%

Conditions

Temperature
130 °C

Procedure

A mixture of 2-ethoxy-5-aminopyridine (2.89 g, 20.9 mmol) and diethyl ethoxymethylenemalonate (4.23 mL, 20.9 mmol) was heated at 130° C. for 4.5 hours. While warm, the mixture was evacuated. After cooling, the product was triturated with 2:1 hexanes:ether and collected to afford 6.04 g of diethyl (2-ethoxy-5-pyridylaminomethylene)malonate as a beige solid.

Workup

  1. temperatureWhile warm
  2. customthe mixture was evacuated
  3. temperatureAfter cooling
  4. customthe product was triturated with 2:1 hexanes
  5. customether and collected

Sources & evidence

ORD record
ord-eed52daa79ca47ec883bf02574915434
Source dataset
uspto-grants-2003_11
Patent number
US06646124B2

Linked notes

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