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

HRID 54170

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HRID 54170 반응식
[CH2:1]([O:3][C:4](=[O:17])[C:5](=[CH:13]OCC)[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=O)[CH3:2].[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:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:17])[CH:13]=1)([O-:20])=[O:19]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

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온도
0 °C

실험 절차

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 then2% 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.

후처리

  1. customThe inorganics are removed by filtration
  2. concentrationthe filtrate is concentrated to an oily solid which
  3. customchromatographed, first with methylene chloride and then2% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-04fbdba3c45840e983b84c4d0744edfa
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622913

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