Diethyl Oxalate → HCID 59753627, compound

HRID 1693346Notes

Reaction equation

HRID 1693346 reaction equation
[O-]CC.[K+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[N:17]=1>C(OCC)C.C(O)C>[CH2:13]([O:12][C:5](=[O:11])[C:6](=[O:8])[CH2:25][C:18]1[N:17]=[C:16]([Cl:15])[CH:21]=[CH:20][C:19]=1[N+:22]([O-:24])=[O:23])[CH3:14]

Participants

6

Reactant 3

HCID 7268Diethyl OxalateHCID 2531236-Chloro-2-methyl-3-nitropyridineHCID 23670592Potassium ethoxide

Product 1

HCID 59753627HCID 59753627, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of potassium ethoxide (134 mg, 1.59 mmol) in diethyl ether (5 mL) and ethanol (1 mL) was added diethyl oxalate (218 μL, 1.59 mmol) in one portion and the resulting solution was stirred for 30 min at rt. 2-Chloro-6-methyl-5-nitropyridine (Preparation 3, 250 mg, 1.45 mmol) was added as a suspension in diethyl ether (2 mL, anhydrous) and stirring was continued for 17 h at rt. The mixture was filtered on a sinter, washing with cold diethyl ether. The collected precipitate was dissolved in glacial acetic acid then evaporated to dryness in vacuo to give the title compound as a brown powder. δH (CDCl3): 1.40 (3H, t, 7.27 Hz), 4.38 (2H, q, 7.25 Hz), 7.33 (1H, d, 8.59 Hz), 7.37 (1H, s), 8.40 (1H, d, 8.86 Hz).

Workup

  1. stirringstirring
  2. waitwas continued for 17 h at rt
  3. filtrationThe mixture was filtered on a sinter
  4. washwashing with cold diethyl ether
  5. dissolutionThe collected precipitate was dissolved in glacial acetic acid
  6. customthen evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-62ef24b64a874bf082f531b5fa26d638
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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