Water → [4-(2-Methylquinolin-4-ylmethoxy)phenyl]carbamic acid tert-butyl ester

HRID 473767Notes

Reaction equation

HRID 473767 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([CH3:13])[CH:4]=1.[C:14]([O:18][C:19](=[O:28])[NH:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)([CH3:17])([CH3:16])[CH3:15].C([O-])([O-])=O.[Cs+].[Cs+].O>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CS(C)=O>[C:14]([O:18][C:19](=[O:28])[NH:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:2][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=[C:5]([CH3:13])[CH:4]=2)=[CH:25][CH:26]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2756771N-Boc-4-hydroxyanilineHCID 115357194-(Chloromethyl)-2-methylquinoline

Product 1

HCID 57562794[4-(2-Methylquinolin-4-ylmethoxy)phenyl]carbamic acid tert-butyl esterYield 73.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 4-chloromethyl-2-methylquinoline (6.84 g, 30.0 mmol), (4-hydroxyphenyl)carbamic acid tert-butyl ester (6.24 g, 30.0 mmol), Cs2CO3 (20.0 g, 60.0 mmol), and n-Bu4NI (11.1 g, 30.0 mmol) in DMSO (150 mL) was stirred at 80° C. for 3 h. The mixture was then cooled, dumped into cold water, and extracted with ethyl acetate. The combined extract was washed with water, brine, dried and concentrated. Chromatograph by CH2Cl2/EtOAc to provide compound [4-(2-methylquinolin-4-ylmethoxy)phenyl]-carbamic acid tert-butyl ester (8.0 g). ESI (M+H)+365.3.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with water, brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7220e578104b43c1975f60d26d4445b7
Source dataset
uspto-grants-2014_01
Patent number
US08637497B2

Reaction notes

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