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

HRID 1609507

反応式

HRID 1609507 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-8163d9ba4b404caaaa340f83b033a8bf
出典データセット
uspto-grants-1995_03
特許番号
US05401751

関連ノート

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