Dimethyl malonate → HCID 2764544, compound

HRID 63411Notes

Reaction equation

HRID 63411 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([O:18][CH3:19])(=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14].[H-].[Na+]>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:12]([C:11]([O:18][CH3:19])=[O:17])[C:13]([O:15][CH3:16])=[O:14])=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydride2×HCID 783082-Chloro-5-nitropyridine

Product 1

HCID 2764544HCID 2764544, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-chloro-5-nitropyridine (25.0 g, 158 mmol) and dimethyl malonate (21.9 g, 166 mmol) in DMF (150 mL) was cooled to 0° C., and sodium hydride (6.50 g of a 60% dispersion in mineral oil, 162 mmol) was added in small portions. The mixture was stirred at 0° C. for 1 hour following completion of the addition. Then, another equivalent of sodium hydride (6.5 g of a 60% dispersion in mineral oil, 162 mmol) was added in small portions. The reaction was quenched by the addition of acetic acid (10 mL), and the mixture was evaporated to dryness. The residue was triturated with diethyl ether (150 mL) overnight and filtered, providing crude dimethyl 2-(5-nitropyridin-2-yl)malonate as an orange solid.

Workup

  1. additioncompletion of the addition
  2. customThe reaction was quenched by the addition of acetic acid (10 mL)
  3. customthe mixture was evaporated to dryness
  4. customThe residue was triturated with diethyl ether (150 mL) overnight
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e6f40d01174d492584d8cc25340a9d6d
Source dataset
uspto-grants-2016_09
Patent number
US09447070B2

Reaction notes

Loading…