Sodium Hydroxide → 7-(Benzyloxy)-4-chloro-6-methoxyquinoline

HRID 2277403Notes

Reaction equation

HRID 2277403 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](O)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:24])=O.[OH-].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:24])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 178486758HCID 178486758, compound

Product 1

HCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-(benzyloxy)-6-methoxyquinolin-4-ol (24.60 g, 87.45 mmol) in toluene (75 mL) was added phosphorus oxychloride (90 mL) slowly. The reaction was heated to reflux for 2 hours, and then cooled to room temperature, diluted with EtOAc (200 mL). The resulted solution was poured into a mixture of ice and 3 N NaOH in portions. The pH of the mixture was adjusted with 3 N NaOH to 7˜8. The organic phase was separated, washed with water (200 mL) followed by brine (100 mL) and concentration in vacuo. The title compound was obtained as a white solid (22.1 g, 84.5%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. customThe organic phase was separated
  4. washwashed with water (200 mL)
  5. concentrationfollowed by brine (100 mL) and concentration in vacuo

Sources & evidence

ORD record
ord-78c40a271d004af89f3d71b5cac3c71a
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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