Water → Methyl 7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 908552ノート

反応式

HRID 908552 の反応式
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5](OC)=[O:6].[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[C:21](=O)[O:20][C:19](=O)[N:18](C)[C:17]=2[CH:25]=1.O>CN(C=O)C>[Br:12][C:13]1[CH:25]=[C:17]2[C:16]([C:21]([OH:20])=[C:4]([C:3]([O:10][CH3:11])=[O:9])[C:5](=[O:6])[N:18]2[CH3:19])=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 962WaterHCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 593401087-Bromo-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

生成物 1

HCID 59340050Methyl 7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate収率 67.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a 50 mL RBF was added sodium hydride (0.15 g, 3.7 mmol) and N,N-dimethylformamide (50 mL, 3.1 mmol) under nitrogen. The mixture was cooled with an ice-water bath for 10 min, and then dimethyl malonate (6.4 mL, 56 mmol) was added over 3 min. A mixture of 7-bromo-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione (0.80 g, 3.1 mmol) in DMF (5.0 mL) was added, and then the reaction was placed in oil bath at 120° C. for 3 hours. The reaction was cooled to room temperature, and water (25 mL) was added to the mixture. A white solid was collected by filtration and washed with water (100 mL), followed by ether (100 mL). The white solid was placed in vacuum oven at 50° C. for 6 h to afford the desired product as a white solid (0.65 g, 67%).

後処理

  1. temperatureThe mixture was cooled with an ice-water bath for 10 min
  2. additionwas added
  3. filtrationA white solid was collected by filtration
  4. washwashed with water (100 mL)
  5. waitThe white solid was placed in vacuum oven at 50° C. for 6 h

出典と根拠

ORDレコード
ord-c0273f428adc4107b9cbed7ba614e807
出典データセット
uspto-grants-2011_09
特許番号
US08017626B2

反応ノート

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