Water → 4-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamine

HRID 15509Notes

Reaction equation

HRID 15509 reaction equation
[F:1][C:2]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.[NH4+].[Cl-].CN(C=O)C.O>CO.C1COCC1.[Zn]>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:17][CH3:18])[N:8]=[CH:7][CH:6]=[C:5]2[O:4][C:3]1[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:2]=1[F:1]

Participants

8

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 114507634-(2-Fluoro-4-nitrophenoxy)-6,7-dimethoxyquinoline

Product 1

HCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineYield 41%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(2-fluoro-4-nitrophenoxy)-6,7-dimethoxyquinoline (612 mg, 1.8 mmol), Zn powder (2.0 g) and NH4Cl (1.4 g) in MeOH (25 mL) and THF (25 mL) was heated at reflux temp. overnight with stirring. To this mixture was added DMF (45 mL) and water (20 mL), stirred for 10 minutes, and the solid was filtered. The filtrate solution was concentrated in vacuo, and the residue was purified by preparative HPLC to afford the product (230 mg, 41%) as a brown solid. 1H NMR (CDCl3) δ 8.38 (d, 1H, J=5.5 Hz), 7.52 (s, 1H), 7.32 (s, 1H), 6.91 (t, 1H, J=8.8 Hz), 6.44 (dd, 1H, J=11.6, 2.2 Hz), 6.38 (dd, 1H, J=8.2, 2.2 Hz), 6.32 (d, 1H, J=5.0 Hz), 3.94 (s, 3H), 3.92 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temp
  3. stirringstirred for 10 minutes
  4. filtrationthe solid was filtered
  5. concentrationThe filtrate solution was concentrated in vacuo
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3e9544f9b2744c92848d45ef2d7335ea
Source dataset
uspto-grants-2010_06
Patent number
US07732613B2

Reaction notes

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