Hydrazine hydrate (1:1) → 9-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one

HRID 519079ノート

反応式

HRID 519079 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=S)[N:15]3[CH:18]([CH3:24])[C:19](OCC)=[O:20])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.O.[NH2:27][NH2:28]>CCO>[CH3:7][C:4]1[N:3]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14]4[N:15]3[CH:18]([CH3:24])[C:19](=[O:20])[NH:27][N:28]=4)=[CH:10][CH:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 86727445ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-thioxo-3,4-dihydroquinolin-1(2H)-yl)propanoate

生成物 1

HCID 867274469-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one収率 81%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-thioxo-3,4-dihydroquinolin-1(2H)-yl)propanoate (0.2 g, 0.561 mmol) in EtOH (10 mL) was added hydrazine hydrate (6 mL) and the solution was heated to reflux overnight. The reaction mixture was cooled to ambient temperature and the solvent was removed in vacuo. Water (10 mL) was added to the residue and the mixture was extracted with EtOAc (2×30 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 30-50% EtOAc in petroleum ether) to give 9-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-5,6-dihydro-1H-[1,2,4]-triazino[4,3-a]quinolin-2(3H)-one (0.14 g, 81%). 1H NMR (CDCl3, 400 MHz): δ 8.04 (brs, 1H), 7.21 (d, J=8.0 Hz, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.73 (s, 1H), 5.89 (s, 2H), 4.56 (q, J=6.8 Hz, 1H), 2.93 (m, 2H), 2.63 (m, 2H), 2.05 (s, 6H), 1.42 (d, J=6.8 Hz, 3H).

後処理

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  3. customthe solvent was removed in vacuo
  4. additionWater (10 mL) was added to the residue
  5. extractionthe mixture was extracted with EtOAc (2×30 mL)
  6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel (eluting with 30-50% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-7b00a39fc7bb4625bbc344f03a7f0a57
出典データセット
uspto-grants-2015_08
特許番号
US09115151B2

反応ノート

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