Hydrochloric Acid → Diethyl 1,6-dihydro-5-nitro-6-oxo-2,3-pyridinedicarboxylate

HRID 864287

反応式

HRID 864287 の反応式
C(O[CH:4]=[C:5]([C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[N+:18]([CH2:21][C:22]([NH2:24])=[O:23])([O-:20])=[O:19].C([O-])(=O)C.[Na+].Cl>C(O)C>[N+:18]([C:21]1[C:22](=[O:23])[NH:24][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=1)([O-:20])=[O:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 40590Diethyl 2-(ethoxymethylidene)-3-oxobutanedioateHCID 2792562-NitroacetamideHCID 517045Sodium Acetate

生成物 1

HCID 19958208Diethyl 1,6-dihydro-5-nitro-6-oxo-2,3-pyridinedicarboxylate収率 79.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
0 °C

実験手順

Diethyl (ethoxymethylene)oxalacetate (5.63 g, 0.023 mol,) is dissolved under N2 atmosphere in 20 mL of absolute ethanol and cooled to 0° C. Nitroacetamide (2.00 g, 0.019 mol,) (S. K. Brownstein, J. Org. Chem 23, 113 (1958)) and sodium acetate (1.56 g, 0.019 mol,) are added and the mixture is stirred at room temperature for 15 hours. The suspension is diluted with 15 mL of absolute ethanol and acidified to pH 2 with concentrated HCl. The inorganics are removed by filtration and the filtrate is concentrated to an oily solid which is gravity chromatographed, first with methylene chloride and then 2% methanol in methylene chloride. The fractions are combined and stripped to give 4.28 g of the title product as a yellow solid, 78.4% yield, melting point 144°-145° C.

後処理

  1. customThe inorganics are removed by filtration
  2. concentrationthe filtrate is concentrated to an oily solid which
  3. customchromatographed, first with methylene chloride

出典と根拠

ORDレコード
ord-0756ebb7cbf04ce494d05983d04836ad
出典データセット
uspto-grants-1996_10
特許番号
US05563113

関連ノート

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