4-Chloro-6-nitroquinoline → 2-Nitroquinoline

HRID 1711350Notes

Reaction equation

HRID 1711350 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) [1.11 g, 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 (APCl+): 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-45886ca7020c440f9ea151f5202eb3c1
Source dataset
uspto-grants-2010_09
Patent number
US07790746B2

Reaction notes

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