Water → 1-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde

HRID 654807

반응식

HRID 654807 반응식
[H-].[Na+].[O:3]=[C:4]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1.[CH3:16]I.O>CN(C)C=O>[CH3:16][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[C:13]([CH:14]=[O:15])[C:4]1=[O:3]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5893342-hydroxyquinoline-3-carbaldehyde

생성물 1

HCID 49146281-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (55% w/w suspension in oil; 0.268 g) was added portionwise to a stirred suspension of 1,2-dihydro-2-oxoquinoline-3-carbaldehyde (1 g) in dimethylformamide (10 ml) which had been cooled in an ice bath. The mixture was allowed to warm to ambient temperature and was then heated to 60° C. for 1 hour. The mixture was recooled in an ice bath and methyl iodide (0.41 ml) was added. Dimethylformamide (50 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was poured into water (50 ml) and extracted with methylene chloride (3×50 ml). The combined extracts were washed with water (50 ml) and evaporated. The residue was triturated under diethyl ether to give 1,2-dihydro-1-methyl-2-oxoquinoline-3-carbaldehyde as a pale yellow solid (0.81 g, 74%).

후처리

  1. temperaturehad been cooled in an ice bath
  2. temperaturewas then heated to 60° C. for 1 hour
  3. customThe mixture was recooled in an ice bath
  4. extractionextracted with methylene chloride (3×50 ml)
  5. washThe combined extracts were washed with water (50 ml)
  6. customevaporated
  7. customThe residue was triturated under diethyl ether

출처 및 근거

ORD 기록
ord-b59bcc54202a457cb5c5df43c06e1275
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05134148

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