Ethanol → (3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl(2,3-dihydro-1H-inden-5-yl)carbamate

HRID 384494ノート

反応式

HRID 384494 の反応式
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11](CO)[C:10]=1[CH3:21])C1C=CC=CC=1.[CH2:22]1[C:30]2[C:25](=[CH:26][C:27]([N:31]=[C:32]=O)=[CH:28][CH:29]=2)[CH2:24][CH2:23]1.C[OH:35].[CH2:36]([OH:38])C>C1COCC1.[Pd]>[CH3:21][C:10]1[C:9](=[O:8])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[O:35][C:36](=[O:38])[N:31]([CH3:32])[C:27]1[CH:26]=[C:25]2[C:30](=[CH:29][CH:28]=1)[CH2:22][CH2:23][CH2:24]2

参加物

7

反応物 4

HCID 702EthanolHCID 887MethanolHCID 50036815-Indanyl isocyanateHCID 68508380[4-(Benzyloxy)-3-methylquinolin-2-yl]methanol

生成物 1

HCID 86646236(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl(2,3-dihydro-1H-inden-5-yl)carbamate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

To a solution of [4-(benzyloxy)-3-methylquinolin-2-yl]methanol (400 mg) in THF (8 mL) was added (5-indanyl)isocyanate (498 mg), and the mixture was stirred at 40° C. for 15 hours. Methanol (2 mL) was added to the reaction liquid to stop the reaction. Ethanol (10 mL) and 10% palladium-activated carbon (200 mg) were added to this mixture. The mixture was stirred at room temperature under hydrogen atmosphere for 30 minutes. The catalyst was removed by filtration, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=98/2) to obtain (3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl(2,3-dihydro-1H-inden-5-yl)carbamate (356 mg).

後処理

  1. customthe reaction
  2. stirringThe mixture was stirred at room temperature under hydrogen atmosphere for 30 minutes
  3. customThe catalyst was removed by filtration
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=98/2)

出典と根拠

ORDレコード
ord-dcdf09814cd54710aa7023cf13887b66
出典データセット
uspto-grants-2013_02
特許番号
US08367702B2

反応ノート

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