Dabco → Methyl-phenyl-carbamic Acid 2-methyl-quinolin-6-yl Ester

HRID 1831326Notes

Reaction equation

HRID 1831326 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.[CH3:13][N:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15](Cl)=[O:16].N12CCN(CC1)CC2>ClCCl>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][C:15](=[O:16])[N:14]([CH3:13])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 5943956-Hydroxy-2-methylquinoline

Product 1

HCID 69519047Methyl-phenyl-carbamic Acid 2-methyl-quinolin-6-yl EsterYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-methylquinolin-6-ol (1.00 g, 6.28 mmol), N-methyl-N-phenylcarbamoyl chloride (1.07 g, 6.28 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.70 g, 6.28 mmol) in dichloromethane (10 mL) was stirred at room temperature for 18 hours. Extra dichloromethane was added and the solution was extracted twice with water, dried over sodium sulphate and filtered. Some ethyl acetate and heptane were added and the solution was slowly evaporated in vacuo yielding the title compound (1.64 g, 89% yield) as a white solid.

Workup

  1. extractionthe solution was extracted twice with water
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. additionSome ethyl acetate and heptane were added
  5. customthe solution was slowly evaporated in vacuo

Sources & evidence

ORD record
ord-447bf91534334cf884ac0bbaadac0176
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

Loading…