Hydrochloric Acid → Dibenzyl 5-nitro-2-pyridylmalonate

HRID 2354045Notes

Reaction equation

HRID 2354045 reaction equation
[C:1]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:13])[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[H-].[Na+].[H][H].Cl[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][N:28]=1.Cl>C1COCC1.C(OCC)(=O)C>[N+:33]([C:30]1[CH:31]=[CH:32][C:27]([CH:2]([C:1]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])=[N:28][CH:29]=1)([O-:35])=[O:34]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 84754Dibenzyl malonateHCID 178418361HCID 178418361, compound

Product 1

HCID 69115439Dibenzyl 5-nitro-2-pyridylmalonateYield 81%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of dibenzyl malonate (2.84 g, 10 mmol) in THF (10 ml) was gradually dropped to sodium hydride (800 mg, 20 mmol: 60%) in THF (20 ml) under a nitrogen atmosphere at room temperature. After cessation of evolution of hydrogen, thereto was gradually added 2-chloro-5-nitropyridine (1.59 g, 10 mmol) in THF (10 ml). The mixture was stirred for 24 hours at room temperature, and then neutralized with 1N hydrochloric acid. The resulted precipitate was dissolved by adding ethyl acetate (200 ml) thereto. The aqueous layer was separated and the organic layer was washed with saturated brine (30 mL), followed by concentration in vacuo. The residue was washed with hexane (50 mL×2) and dried to give the object compound (8) as an orange solid (3.29 g, yield 81%).

Workup

  1. dissolutionThe resulted precipitate was dissolved
  2. customThe aqueous layer was separated
  3. washthe organic layer was washed with saturated brine (30 mL)
  4. concentrationfollowed by concentration in vacuo
  5. washThe residue was washed with hexane (50 mL×2)
  6. customdried

Sources & evidence

ORD record
ord-10091e72543842b89ae8b32e1cb46376
Source dataset
uspto-grants-2010_07
Patent number
US07750162B2

Reaction notes

Loading…