N-Methylethylenediamine → 1-Methyl-3-(4-nitrophenyl)-5,6-dihydropyrazin-2(1H)-one

HRID 1772078노트

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HRID 1772078 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:17])C(OCC)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:18][NH:19][CH2:20][CH2:21][NH2:22]>CO>[CH3:18][N:19]1[CH2:20][CH2:21][N:22]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[C:11]1=[O:17]

참가 물질

4

반응물 2

HCID 8014N-MethylethylenediamineHCID 15716402Ethyl 4-nitrophenylpyruvate

생성물 1

HCID 666138231-Methyl-3-(4-nitrophenyl)-5,6-dihydropyrazin-2(1H)-one수율 20%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with ethyl 4-nitrophenylpyruvate (5.00 g, 22.4 mmol) and anhydrous methanol (112 mL). The resulting solution was cooled to 0° C. with an ice bath, and N-methylethylenediamine (1.66 g, 22.4 mmol) was added dropwise. After addition was complete, the bath was removed and the reaction was stirred at room temperature for 18 h. After this time the reaction was concentrated under reduced pressure. The residue was purified by column chromatography to afford 1-methyl-3-(4-nitrophenyl)-5,6-dihydropyrazin-2(1H)-one (102h) in 20% yield (1.02 g) as a yellow solid: mp 191-192° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.26 (d, 2H, J=6.9 Hz), 8.05 (d, 2H, J=7.2 Hz), 3.94 (t, 2H, J=6.3 Hz), 3.55 (t, 2H, J=6.3 Hz), 3.02 (s, 3H); MS (ESI+) m/z 234.1 (M+H).

후처리

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. additionAfter addition
  4. customthe bath was removed
  5. concentrationAfter this time the reaction was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-78f75b24a5624e278b4817b85c3d926a
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249123B2

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