Diethyl Oxalate → potassium (1Z)-1-[2-(dibenzylamino)-3-nitropyridin-4-yl]-3-ethoxy-3-oxoprop-1-en-2-olate
Reaction equation
[O-]CC.[K+:4].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[CH2:15]([N:22]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[C:27]([CH3:32])[CH:26]=[CH:25][N:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)C>[CH2:33]([N:22]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[C:27](/[CH:32]=[C:6](\[O-:8])/[C:5]([O:12][CH2:13][CH3:14])=[O:11])[CH:26]=[CH:25][N:24]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1.[K+:4]Participants
Procedure
A slurry of potassium ethoxide (391 mg, 4.64 mmol) in diethyl ether (4 mL) under N2 was cooled to 0° C. under vigorous stirring. Diethyl oxalate (0.63 mL, 4.65 mmol) was added, and the mixture was stirred for 5 min. A solution of 2-(dibenzylamino)-4-methyl-3-nitropyridine (1.52 g, 4.56 mmol) in diethyl ether (3 mL) was added, and the mixture was stirred for 16 h while slowly warming to room temperature, during which time a precipitate formed. The solid was collected on a sintered glass frit and rinsed several times with additional diethyl ether. The solid was transferred to a vial and dried under vacuum at 30° C. for 2 h to provide potassium (1Z)-1-[2-(dibenzylamino)-3-nitropyridin-4-yl]-3-ethoxy-3-oxoprop-1-en-2-olate (1.63 g, 3.46 mmol, 76%) as a light orange solid. This product was immediately used without purification or identification.
Workup
- stirringthe mixture was stirred for 16 h
- customformed
- customThe solid was collected on a sintered glass frit
- washrinsed several times with additional diethyl ether
- customdried under vacuum at 30° C. for 2 h
Sources & evidence
- ORD record
- ord-2da7aaa754514e7e85183d8bd414b168
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608627B2
Reaction notes
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