Sodium Bicarbonate → 4-Chloroquinolin-7-ol

HRID 454034Notes

Reaction equation

HRID 454034 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:19])=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(O)(C(F)(F)F)=O>[Cl:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=2)[N:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 220306577-(Benzyloxy)-4-chloroquinoline

Product 1

HCID 1357290834-Chloroquinolin-7-olYield 98%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-4-chloroquinoline (17 g, 56 mmol), (Konishi et al. WO 96/11187), in TFA (170 ml) was heated at reflux for 2 hours. The solvent was removed under vacuum and the residue was triturated with ether, filtered and washed with ether. The solid was suspended in an aqueous solution of sodium hydrogen carbonate (5.5 g, 65 mmol in 200 ml of water) and stirred at ambient temperature for 30 minutes. The solid was collected by filtration, washed with water and dried overnight under vacuum and over phosphorus pentoxide to give 4-chloro-7-hydroxyquinoline (9.85 g, 98%).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed under vacuum
  3. customthe residue was triturated with ether
  4. filtrationfiltered
  5. washwashed with ether
  6. filtrationThe solid was collected by filtration
  7. washwashed with water
  8. dry with materialdried overnight under vacuum and over phosphorus pentoxide

Sources & evidence

ORD record
ord-81d96576094948048c93a9a5dc4063b5
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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