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

HRID 908552노트

반응식

HRID 908552 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 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 67.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c0273f428adc4107b9cbed7ba614e807
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017626B2

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