Diethyl (ethoxymethylene)malonate → Ethyl 4-Hydroxy-6,8-dimethyl-1,7-naphthyridine-3-carboxylate

HRID 411228

반응식

HRID 411228 반응식
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C([O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>C1(C)C(C)=CC=CC=1>[OH:12][C:13]1[C:6]2[C:7](=[C:2]([CH3:1])[N:3]=[C:4]([CH3:9])[CH:5]=2)[N:8]=[CH:20][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

참가 물질

4

반응물 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 769642,6-Dimethyl-3-pyridylamine

생성물 1

HCID 22397159Ethyl 4-Hydroxy-6,8-dimethyl-1,7-naphthyridine-3-carboxylate수율 30%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

A mixture of 2,6-dimethyl-3-aminopyridine (0.85 g) and diethyl ethoxymethylenemalonate (1.53 g) is heated at 135° C. in xylene (30 mL) for 2 h allowing for removal of ethanol. After the solvent is removed, the mixture is suspended in diphenyl ether (15 mL). The mixture is then heated to reflux with removal of ethanol for 30 min. The reaction mixture is cooled to room temperature and hexanes (20 mL) is added. The resulting precipitate is filtered, washed with diethyl ether (2×10 mL) and dried to give 0.5 g (30%) of the title compound as a brown solid. Physical chracteristics: MS (ESI+) m/z 247 (M+H)+; 1H NMR (DMSO) δ 8.67, 7.97,4.38, 2.85,2.67, 1.40.

후처리

  1. customallowing for removal of ethanol
  2. customAfter the solvent is removed
  3. temperatureThe mixture is then heated
  4. temperatureto reflux with removal of ethanol for 30 min
  5. additionhexanes (20 mL) is added
  6. filtrationThe resulting precipitate is filtered
  7. washwashed with diethyl ether (2×10 mL)
  8. customdried

출처 및 근거

ORD 기록
ord-49a08db830dd47799eff0645827e3280
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559145B2

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