4-Chloro-6-nitroquinoline → 2-Nitroquinoline

HRID 547531Notes

Reaction equation

HRID 547531 reaction equation
[Cl-].[Cl-].[NH3+]C1C=CC(C(N[C:11]2[CH:24]=[CH:23][C:14]([NH:15][C:16]3[CH:21]=[CH:20][N+](C)=CC=3)=[CH:13][CH:12]=2)=O)=CC=1.ClC1C2C(=CC=C([N+:38]([O-:40])=[O:39])C=2)N=CC=1>CO.Cl>[N+:38]([C:16]1[CH:21]=[CH:20][C:13]2[C:14](=[CH:23][CH:24]=[CH:11][CH:12]=2)[N:15]=1)([O-:40])=[O:39]

Participants

5

Reactant 2

HCID 2872104-Chloro-6-nitroquinolineHCID 671991294-{4-[(4-Ammoniobenzoyl)amino]anilino}-1-methylpyridinium dichloride

Product 1

HCID 877592-Nitroquinoline

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a suspension of amide B7 (2.09 g, 5.32 mmol) in dry MeOH (100 mL) were sequentially added 4-chloro-6-nitroquinoline (F1) [1.11g, 5.32 mmol] and a few drops of concentrated HCl, and the resultant mixture was refluxed for 12 h. After this time, solvent was removed under reduced pressure, and the residue was re-suspended in 1:1 MeOH:EtOAc. This mixture was heated to remove MeOH, and then cooled, and the resulting precipitate collected by filtration. This solid was recrystallized from MeOH:EtOH to give nitroquinoline Cpd. G (2.48 g, 89%) as an amorphous yellow solid; 1H NMR [CD3)2SO]: δ 3.96 (s, 3H, R2N+−CH3), 7.12 (m, 3H, ArH), 7.35 (d, J=8.81 Hz, 2H, ArH), 7.68 (d, J=8.51 Hz, 2H, ArH), 7.96 (d, J=8.81 Hz, 2H ArH), 8.24 (m, 5H, ArH), 8.72 (m, 2H, ArH), 9.83 (d, J=1.69 Hz, 1H, ArH), 10.56 (s, 1H, ArNHAr), 10.67 (s, 1H, ArNHAr), 11.48 (br s, 1H, ArNHAr). LCMS (APCI+): 492 (20%).

Workup

  1. customAfter this time, solvent was removed under reduced pressure
  2. temperatureThis mixture was heated
  3. customto remove MeOH
  4. temperaturecooled
  5. filtrationthe resulting precipitate collected by filtration
  6. customThis solid was recrystallized from MeOH

Sources & evidence

ORD record
ord-b3ba06cc457c43e1a6c5daa98328029f
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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