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4-Nitrophenol → 4-[(2-Methyl-4-quinolinyl)methoxy]benzenamine dihydrochloride

HRID 1071380
Notes
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Reaction equation

HRID 1071380 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-])=O.[Cl:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([CH3:23])[CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[Cl:32][Sn]Cl>C1COCC1>[ClH:11].[ClH:32].[CH3:23][C:15]1[CH:14]=[C:13]([CH2:12][O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 24479Stannous ChlorideHCID 115357194-(Chloromethyl)-2-methylquinoline

Product 1

HCID 673055374-[(2-Methyl-4-quinolinyl)methoxy]benzenamine dihydrochloride

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitrophenol (7.2 g, 52.0 mmol) in 400 mL THF was added 4-(chloromethyl)-2-methylquinoline (10.0 g, 52.0 mmol), cesium carbonate (25.4 g, 78 mmol), and sodium iodide (451 mg, 3 mmol). The reaction was heated to reflux for 24 hr, after which the reaction was extracted from sat KH2PO4 with EtOAc×3. The combined organic layers were dried with MgSO4, filtered, and concentrated. This residue was taken up in 200 mL MeOH and refluxed with SnCl2 (156 mmol) for 18 hr after which, the solution was cooled and the reaction was extracted from disodium tartrate with EtOAc×4, the combined organic layers were dried with MgSO4, filtered, and concentrated. The residue was treated with 2 M HCl in dioxane, rotovapped, and recrystallized from EtOH/water to give 12.4 g (71%). MS found: (M+H)=265.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 24 hr
  3. extractionafter which the reaction was extracted
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. temperaturethe solution was cooled
  8. extractionthe reaction was extracted from disodium tartrate with EtOAc×4
  9. dry with materialthe combined organic layers were dried with MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. additionThe residue was treated with 2 M HCl in dioxane
  13. customrecrystallized from EtOH/water
  14. customto give 12.4 g (71%)

Sources & evidence

ORD record
ord-2541610dc41b4ce5ab6a55ca14cf2e59
Source dataset
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06906053B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes