HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 15515
Notes
Print preview

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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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' catalystCatalyst
HCID 8857
Ethyl Acetate
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732613B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes