Pentyl chloroformate → Pentyl [(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]carbamate

HRID 384491Notes

Reaction equation

HRID 384491 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH3:15])=[CH:11][CH:10]=[CH:9][CH:8]=2.Cl[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:19]>N1C=CC=CC=1>[CH3:15][C:14]1[C:13](=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH2:4][NH:3][C:18](=[O:19])[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 69489Pentyl chloroformateHCID 685107592-(aminomethyl)-3-methylquinolin-4(1H)-one dihydrochloride

Product 1

HCID 59526959Pentyl [(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]carbamateYield 56.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(aminomethyl)-3-methylquinolin-4(1H)-one dihydrochloride (160 mg) in pyridine (8 mL) was added pentyl chloroformate (100 mg), followed by stirring at room temperature for 6 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (eluent: chloroform/methanol) to obtain pentyl [(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]carbamate (104 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-0fadd6803b19479cb0949f9f31d07a64
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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