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

HRID 384494Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-dcdf09814cd54710aa7023cf13887b66
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367702B2

Reaction notes

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