4-(1-tert-Butoxypropan-2-yloxy)-7-methoxyquinoline → 2-(7-Methoxyquinolin-4-yloxy)propan-1-ol

HRID 1878697Notes

Reaction equation

HRID 1878697 reaction equation
C([O:5][CH2:6][CH:7]([O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1)[CH3:8])(C)(C)C>C(O)(C(F)(F)F)=O>[CH3:21][O:20][C:16]1[CH:15]=[C:14]2[C:19]([C:10]([O:9][CH:7]([CH3:8])[CH2:6][OH:5])=[CH:11][CH:12]=[N:13]2)=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 598430204-(1-tert-Butoxypropan-2-yloxy)-7-methoxyquinoline

Product 1

HCID 688094362-(7-Methoxyquinolin-4-yloxy)propan-1-ol

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(1-tert-butoxypropan-2-yloxy)-7-methoxyquinoline in TFA (10 mL) was stirred for 45 min at 23° C. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and 10% Na2CO3. The aqueous layer was extracted with CH2Cl2 (5 mL×4) and the combined organics were dried over MgSO4. The mixture was purified on 12 grams of silica eluting with 0-100% of 5% MeOH/CH2Cl2. MS (ESI pos. ion) m/z (MH+): 234. Calc'd exact mass for C13H15NO3: 233.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 and 10% Na2CO3
  3. extractionThe aqueous layer was extracted with CH2Cl2 (5 mL×4)
  4. dry with materialthe combined organics were dried over MgSO4
  5. customThe mixture was purified on 12 grams of silica eluting with 0-100% of 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-1574bb056f6043b1b9eaf6ec7fbce1a0
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

Loading…