Diethyl Oxalate → Ethyl 3-(2-chloro-5-nitropyridin-4-yl)-2-oxopropanoate

HRID 751612Notes

Reaction equation

HRID 751612 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12](OCC)(=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].N12CCCN=C1CCCCC2>COC(C)(C)C.O.C(O)(=O)C>[CH2:16]([O:15][C:13](=[O:14])[C:12](=[O:18])[CH2:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1)[CH3:17]

Participants

7

Reactant 3

HCID 7268Diethyl OxalateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 53472030Ethyl 3-(2-chloro-5-nitropyridin-4-yl)-2-oxopropanoate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Route B: To a solution of 2-chloro-4-methyl-5-nitropyridine (1.0 g, 5.8 mmol) in diethyl oxalate (4.23 g, 29 mmol) under an argon atmosphere was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.95 mL, 6.4 mol). The mixture was stirred at rt for 1.5 h then diluted with t-butyl methyl ether (40 mL), water (30 mL) and acetic acid (1 ml). The organic layer was separated, washed with water, dried (MgSO4) and evaporated to dryness. The resultant damp red solid residue was finally dried under high vacuum at 40–50° C. to give the title compound.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customThe resultant damp red solid residue was finally dried under high vacuum at 40–50° C.

Sources & evidence

ORD record
ord-a31ae5a53bb541c9b0d9c375682bc0a2
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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