Isobutylene oxide → 2-Methyl-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol

HRID 2277384Notes

Reaction equation

HRID 2277384 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].[CH3:24][C:25]1([O:28][CH2:27]1)[CH3:26]>O>[CH3:24][C:25]([OH:28])([CH3:27])[CH2:26][O:19][C:15]1[CH:14]=[C:13]2[C:18]([C:9]([O:8][C:7]3[CH:20]=[CH:21][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[CH:10][CH:11]=[N:12]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11208Isobutylene oxide2×HCID 14798Sodium HydroxideHCID 1363502994-(4-Nitrophenoxy)quinolin-7-ol

Product 1

HCID 681942572-Methyl-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-olYield 42.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To a flask containing 4-(4-nitrophenoxy)quinolin-7-ol (14.45 g, 45.33 mmol) was added a solution of sodium hydroxide (3.63 g, 90.66 mmol) in water/95% EtOH (90 mL/10 mL) followed by isobutylene oxide (12.12 mL, 136 mmol, pre-cooled to 0° C.). After stirring at 45° C. for 10 minutes, more isobutylene oxide (12.12 mL, 136 mmol, pre-cooled to 0° C.) was added. The reaction was continued to stir for additional 12 hours. The mixture was cooled to room temperature and continued to stir for 4 hours, then cooled to 0° C. and stirred for additional 10 minutes. The resulted solid was filtered, and then dissolved in DCM (130 mL). The solution was filtered and concentrated in vacuo. The residue was washed with petroleum ether (30 mL), and dried in vacuo at 45° C. overnight to afford the title compound as a yellow solid (6.86 g, 42.7%).

Workup

  1. stirringto stir for additional 12 hours
  2. temperatureThe mixture was cooled to room temperature
  3. stirringto stir for 4 hours
  4. temperaturecooled to 0° C.
  5. stirringstirred for additional 10 minutes
  6. filtrationThe resulted solid was filtered
  7. dissolutiondissolved in DCM (130 mL)
  8. filtrationThe solution was filtered
  9. concentrationconcentrated in vacuo
  10. washThe residue was washed with petroleum ether (30 mL)
  11. customdried in vacuo at 45° C. overnight

Sources & evidence

ORD record
ord-70c6776d94694798a3aa9559fd275461
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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