Acetic Acid → Methyl 2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate

HRID 230755노트

반응식

HRID 230755 반응식
[C:1]1([NH:7]/[CH:8]=[CH:9]/[CH:10]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[C:12](OC)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C(O)(=O)C>CO>[O:13]=[C:12]1[C:11]([C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=[CH:8][N:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 24758Sodium hydride2회HCID 59852887(E)-Dimethyl 2-(3-(phenylamino)allylidene)malonate

생성물 1

HCID 59852857Methyl 2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate수율 92.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of (E)-dimethyl 2-(3-(phenylamino)allylidene)malonate (130 mg, 0.50 mrnol) in methanol (8 mL) at rt was added NaH (50 mg of the 60% NaH in oil, 1.2 mmol) and the mixture was stirred at rt for 3 h. Acetic acid (0.3 mL) was added to the mixture, concentrated to a volume of 4 mL, and purificationof the reaction mixture by preparative HPLC provided the desired product (105 mg, 92%) as a yellow solid. 1H NMR (CD3OD) δ 8.30 (dd, 1H, J=7.2, 2.2 Hz), 7.87 (dd, 1H, J=6.6, 1.7 ), 7.57-7.38 (m, 5H), 6.53 (t, 1H, J=7.0 Hz), 3.84 (s, 3H); MS(ESI+) m/z 230.3 (M+H)+.

후처리

  1. concentrationconcentrated to a volume of 4 mL

출처 및 근거

ORD 기록
ord-27163c00b8f645abae144b6820a6c023
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566784B2

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