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

HRID 553545ノート

反応式

HRID 553545 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])O[C:8](=[O:12])[N:7]([CH3:13])[C:6]=2[CH:14]=1.[H-].[Na+].CN(C=O)C.BrC1C=C[C:26]2[C:31](=[O:32])[O:30][C:29](=O)NC=2C=1.IC>O>[Br:1][C:2]1[CH:14]=[C:6]2[C:5]([C:10]([OH:11])=[C:26]([C:31]([O:30][CH3:29])=[O:32])[C:8](=[O:12])[N:7]2[CH3:13])=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 115215774-Bromoisatoic anhydrideHCID 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 74%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

7-Bromo-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione. Sodium hydride (0.47 g, 12 mmol) was added to a 3 neck 250 mL round bottom flask under nitrogen and then washed with hexanes. Once the hexanes were decanted, DMF (20.0 mL, 11 mmol) was added. The resulting mixture was cooled to 0° C. using an ice-water bath, and then 7-bromo-1H-benzo[d][1,3]oxazine-2,4-dione (2.7 g, 11 mmol) was added in one batch. After stirring at room temperature for 1 hour, iodomethane (0.70 mL, 11 mmol) was added dropwise to the yellow solution, and the reaction mixture was stirred for 16 hours. Water (50 mL) was added, and the resulting precipitate that formed was collected via filtration. The solid was washed with additional water (100 mL), followed by ether (100 mL). Drying in a vacuum oven overnight at 50° C. provided the title compound as an off-white solid (2.1 g, 74% yield).

後処理

  1. washwashed with hexanes
  2. customOnce the hexanes were decanted
  3. stirringthe reaction mixture was stirred for 16 hours
  4. customthe resulting precipitate that formed
  5. filtrationwas collected via filtration
  6. washThe solid was washed with additional water (100 mL)
  7. customDrying in a vacuum oven overnight at 50° C.

出典と根拠

ORDレコード
ord-c49bd567fb9747fcab1326c636d8d23c
出典データセット
uspto-grants-2011_11
特許番号
US08048894B2

反応ノート

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