Methanol → 4-(7-(Benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorobenzenamine

HRID 15515Notes

Reaction equation

HRID 15515 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][C:21]=3[F:29])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.CO>CCOC(C)=O.O=[Pt]=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=3[F:29])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 1140TolueneHCID 229354107-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline

Product 1

HCID 597920394-(7-(Benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorobenzenamineYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-(benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline (125 mg, 0.3 mmol) and PtO2 in EtOAc (15 mL) was stirred at rt under 1 atm of H2 gas for 2 h. Toluene (4 mL) and MeOH (5 mL) were added to the reaction mixture, stirred for 20 minutes, filtered the catalyst, and the filtrate solution was concentrated in vacuo to obtain the product (117 mg, 100%) as a white solid. 1H NMR (DMF-d7) δ 8.52 (d, 1H, J=5.0 Hz), 7.68-6.67 (m, 12H), 6.48 (d, 1H, J=5.0 Hz), 5.38 (s, 2H), 4.02 (s, 3H).

Workup

  1. stirringstirred for 20 minutes
  2. filtrationfiltered the catalyst
  3. concentrationthe filtrate solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2c66eb95b2e5493a9d8abd7aad4cfeda
Source dataset
uspto-grants-2010_06
Patent number
US07732613B2

Reaction notes

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