Diethyl (ethoxymethylene)malonate → Diethyl 2-((5-bromopyridin-3-ylamino)methylene)malonate

HRID 1042760Notes

Reaction equation

HRID 1042760 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 67318826Diethyl 2-((5-bromopyridin-3-ylamino)methylene)malonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 500 mL RBF containing 5-bromopyridin-3-amine (60.0 g, 347 mmol) was added diethyl 2-(ethoxymethylene)malonate (71.0 mL, 354 mmol) and 121 mL of toluene. The reaction mixture was heated to reflux for 3 h. The reaction mixture was allowed to cool RT overnight, and the resulting precipitate was collected by filtration and dried to give the desired product as a white crystalline solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-9a7db7a746b2496991a6e1cfcc029cbc
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

Loading…