Hydrochloric Acid → 2-(5-Methyl-3-nitro-pyridin-2-yl)-malonic acid diethyl ester

HRID 1838302

반응식

HRID 1838302 반응식
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([CH3:24])=[CH:17][N:16]=1.Cl>COCCOC>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([CH3:24])=[CH:17][N:16]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 8183002-Chloro-5-methyl-3-nitropyridine

생성물 1

HCID 600601582-(5-Methyl-3-nitro-pyridin-2-yl)-malonic acid diethyl ester

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매3회

실험 절차

A solution of diethyl malonate (72 g, 0.436 mol) in DME (200 mL) is added dropwise to a magnetically stirred suspension of NaH (23 g, 0.58 mol) in dry 1,2-dimethoxyethane (DME, 350 mL). The mixture is stirred at room temperature for 1 hour and then a solution of 2-chloro-5-methyl-3-nitro-pyridine (50 g, 0.290 mol) in DME (100 mL) is added to give a dark red solution. After stirring for 18 hours, the reaction mixture is poured into ice-cold water and acidified to pH 3 with 6N HCl solution. The mixture is extracted with ethyl acetate. The organic phase is washed with water, brine, dried over Na2SO4, and concentrated. The excess diethymalonate is removed at 50° C. under high vacuum to give 2-(5-Methyl-3-nitro-pyridin-2-yl)-malonic acid diethyl ester i as a dark red-colored thick residue; 1H NMR (300 MHz, CDCl3) δ 1.28 (t, J=9 Hz, 6H), 4.26 (q, J=9 Hz, 4H), 8.27 (s, 1H), 8.63 (s, 1H).

후처리

  1. customto give a dark red solution
  2. stirringAfter stirring for 18 hours
  3. additionthe reaction mixture is poured into ice-cold water
  4. extractionThe mixture is extracted with ethyl acetate
  5. washThe organic phase is washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe excess diethymalonate is removed at 50° C. under high vacuum

출처 및 근거

ORD 기록
ord-3c1db0c2ddf84dc89146cc6969e4ea06
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06673811B1

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