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

HRID 1772078ノート

反応式

HRID 1772078 の反応式
[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]

参加物

4

反応物 2

HCID 8014N-MethylethylenediamineHCID 15716402Ethyl 4-nitrophenylpyruvate

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-78f75b24a5624e278b4817b85c3d926a
出典データセット
uspto-grants-2016_02
特許番号
US09249123B2

反応ノート

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