Dimethyl [(dimethylamino)methylidene]propanedioate → HCID 67257898, compound

HRID 1619380Notes

Reaction equation

HRID 1619380 reaction equation
[CH3:1][N:2]([CH:4]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:6]([O:8][CH3:9])=[O:7])C.[Br:14][C:15]1[CH:20]=C[N:18]=[C:17](N)[CH:16]=1>CC(O)=O.O>[Br:14][C:15]1[CH:16]=[CH:17][N:18]=[C:1]([NH:2][CH:4]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:6]([O:8][CH3:9])=[O:7])[CH:20]=1

Participants

5

Reactant 2

HCID 593603Dimethyl [(dimethylamino)methylidene]propanedioateHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 67257898HCID 67257898, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of dimethyl 2-((dimethylamino)methylene)malonate (11.5 g, 65 mmol, 2.2 equiv) and 4-bromopyridin-2-amine (5 g, 28.9 mmol, 1 equiv) in AcOH (40 mL) was stirred at room temperature for 24 h. Then the reaction mixture was diluted with water, filtered, the filter cake was dried to give 4.8 g of the desired product. MS (ESI): 315, 317 (MH+).

Workup

  1. filtrationfiltered
  2. customthe filter cake was dried

Sources & evidence

ORD record
ord-69cdfced59f44692aa96bf80d213db13
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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