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

HRID 553545노트

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HRID 553545 반응식
[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

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 115215774-Bromoisatoic anhydrideHCID 593401087-Bromo-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

생성물 1

HCID 59340050Methyl 7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate수율 74%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-c49bd567fb9747fcab1326c636d8d23c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048894B2

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