Hydrochloric Acid → N-(5-Bromo-2-morpholinophenyl)-8-chloro-2,3-dimethylquinolin-4-amine

HRID 1431299Notes

Reaction equation

HRID 1431299 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[CH3:14].[Br:15][C:16]1[CH:17]=[CH:18][C:19]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[C:20]([NH2:22])[CH:21]=1.Cl.O1CCOCC1>CO>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[C:20]([NH:22][C:2]2[C:11]3[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:13])[C:3]=2[CH3:14])[CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 49618715-Bromo-2-morpholin-4-ylanilineHCID 596315464,8-Dichloro-2,3-dimethylquinoline

Product 1

HCID 59631074N-(5-Bromo-2-morpholinophenyl)-8-chloro-2,3-dimethylquinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to Procedure K, Method 1 using 4,8-dichloro-2,3-dimethylquinoline (104 mg, 460 μmol), 5-bromo-2-morpholinobenzenamine (118 mg, 460 μmol) and 4N hydrochloric acid solution in dioxane (0.050 mL, 200 μmol) in MeOH (1.00 mL) to afford a colorless solid upon purification by chromatography on silica gel, eluting with a Et2O gradient in toluene. 1H NMR (400 MHz, chloroform-d) δ ppm 7.69 (1H, dd, J=7.4, 1.2 Hz), 7.55-7.63 (1H, m), 7.23-7.30 (1H, m), 6.92-6.98 (1H, m), 6.85-6.92 (1H, m), 6.83 (1H, s), 6.18 (1H, d, J=2.3 Hz), 3.80-3.91 (4H, m), 2.92-3.08 (4H, m), 2.71-2.78 (3H, m), 2.23 (3H, s).

Workup

  1. customPrepared
  2. customto afford a colorless solid
  3. customupon purification by chromatography on silica gel
  4. washeluting with a Et2O gradient in toluene

Sources & evidence

ORD record
ord-cfdecc91641241509d459698601fe9de
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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