7-(6-(benzyloxy)-7-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine → 4-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-7-methoxyquinolin-6-ol

HRID 1712977Notes

Reaction equation

HRID 1712977 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2[O:21][C:22]1[CH:23]=[CH:24][C:25]2[NH:30][CH2:29][CH2:28][O:27][C:26]=2[CH:31]=1)C1C=CC=CC=1>C(O)C.[Pd]>[O:27]1[CH2:28][CH2:29][NH:30][C:25]2[CH:24]=[CH:23][C:22]([O:21][C:12]3[C:11]4[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([OH:8])[CH:10]=4)[N:15]=[CH:14][CH:13]=3)=[CH:31][C:26]1=2

Participants

4

Reactant 1

HCID 577371437-(6-(benzyloxy)-7-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine

Product 1

HCID 577371514-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-7-methoxyquinolin-6-olYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

Palladium, 10 wt % on activated carbon (0.100 g, 0.940 mmol) was added to a solution of 7-(6-(benzyloxy)-7-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine (1.156 g, 2.79 mmol) in ethanol (20.0 mL). The system was evacuated and purged with hydrogen (g) three times and then stirred under a H2 (g) atmosphere for 18 h. Additional palladium, 10 wt % on activated carbon (0.100 g, 0.940 mmol) was added to the reaction mixture. The system was evacuated and purged with hydrogen (g) three times and then stirred under a H2 (g) atmosphere for 20 h. The reaction mixture was filtered through a pad of Celite and concentrated to afford an orange brown solid. This material was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-100% (90:10:1, dichloromethane/methanol/ammonium hydroxide)-dichloromethane) to afford 4-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-7-methoxyquinolin-6-ol (0.733 g, 81.0% yield) as a yellow solid. MS (MH+) 325.0; Calculated 324 for C18H16N2O4.

Workup

  1. customThe system was evacuated
  2. custompurged with hydrogen (g) three times
  3. customThe system was evacuated
  4. custompurged with hydrogen (g) three times
  5. stirringstirred under a H2 (g) atmosphere for 20 h
  6. filtrationThe reaction mixture was filtered through a pad of Celite
  7. concentrationconcentrated
  8. customto afford an orange brown solid
  9. customThis material was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-100% (90:10:1, dichloromethane/methanol/ammonium hydroxide)-dichloromethane)

Sources & evidence

ORD record
ord-0902dca8c19847a19c2c81379c4b8c1f
Source dataset
uspto-grants-2010_09
Patent number
US07795254B2

Reaction notes

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