Diethyl Oxalate → HCID 59753627, compound

HRID 751602Notes

Reaction equation

HRID 751602 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-f2970bdc368c4eb7b5d63068f2b925af
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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