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

HRID 1712974Notes

Reaction equation

HRID 1712974 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[CH:22][C:23]4[NH:28][CH2:27][CH2:26][O:25][C:24]=4[CH:29]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])C1C=CC=CC=1>C(O)C.[Pd]>[O:25]1[CH2:26][CH2:27][NH:28][C:23]2[CH:22]=[CH:21][C:20]([O:19][C:13]3[C:12]4[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:30][CH3:31])[CH:11]=4)[N:16]=[CH:15][CH:14]=3)=[CH:29][C:24]1=2

Participants

4

Reactant 1

HCID 577371497-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine

Product 1

HCID 1359667514-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-6-methoxyquinolin-7-olYield 102.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium, 10 wt % on activated carbon (0.050 g, 0.47 mmol) was added to a solution of 7-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine (0.250 g, 0.60 mmol) in ethanol (10.0 mL). 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 4-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-6-methoxyquinolin-7-ol (0.200 g, 102% yield) as a yellow-green solid. MS (MH+) 325.0; Calculated 324 for C18H16N2O4.

Workup

  1. customThe system was evacuated
  2. custompurged with hydrogen (g) three times
  3. filtrationThe reaction mixture was filtered through a pad of Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fbda84616ed848c18546fa7cbe817124
Source dataset
uspto-grants-2010_09
Patent number
US07795254B2

Reaction notes

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