2-Bromopropane → 5,7-dichloro-2-methylamino-8-isopropoxy-quinoline

HRID 872232Notes

Reaction equation

HRID 872232 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:14][CH3:15])=[N:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH:23]([CH3:25])[CH3:24].[Cl-].[NH4+]>CS(C)=O>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([O:13][CH:23]([CH3:25])[CH3:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:14][CH3:15])=[N:7]2

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 116659195,7-Dichloro-2-methylamino-8-hydroxyquinoline

Product 1

HCID 115872985,7-dichloro-2-methylamino-8-isopropoxy-quinolineYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5,7-dichloro-2-methylamino-8-hydroxyquinoline (1.02 g, 4.21 mmol), anhydrous potassium carbonate (2.4 g) and 2-bromopropane (0.6 mL) in dimethyl sulphoxide (10 mL) was stirred at RT for 2 days. Saturated ammonium chloride solution was added and the mixture was extracted with dichloromethane (30 mL×3). The extracts were combined, dried, and concentrated. The residue, after column chromatography (silica gel, dichloromethane), gave 5,7-dichloro-2-methylamino-8-isopropoxy-quinoline 11 as an off-white solid (938 mg, 78%). 1H NMR (CDCl3): δ 8.13 (d, J=9.0, 1 H), 7.28 (s, 1 H), 6.69 (d, J=9.0, 1 H), 5.10 (m, 1 H), 4.90 (br, 1 H), 3.11 (d, J=5.0, 3 H), 1.43 (s, 3 H), 1.41 (s, 3 H).

Workup

  1. extractionthe mixture was extracted with dichloromethane (30 mL×3)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2d06cb73cb8e46898cade14643b27257
Source dataset
uspto-grants-2015_03
Patent number
US08975278B2

Reaction notes

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