Hydrochloric Acid → 6-Bromo-4-chloroquinoline hydrochloride

HRID 1952286Notes

Reaction equation

HRID 1952286 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[Cl:12].Cl.C(OCC)C>C1COCC1>[ClH:12].[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[Cl:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 667822766-Bromo-4-chloroquinoline hydrochlorideYield 200.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure of Wolf, Christian et al. (SynLett 2003 12, 1801-1804), to a solution of 6-bromo-4-chloroquinoline (30 g, 0.124 mol) in anhydrous THF (500 mL) was added 2 M HCl in diethylether (74 mL, 0.148 mol). A white precipitate formed immediately. After stirring for 30 min, the suspension was concentrated in vacuo and dried under vacuum to provide 6-bromo-4-chloroquinoline hydrochloride as an off-white solid (34.6 g, quantitative yield).

Workup

  1. customA white precipitate formed immediately
  2. concentrationthe suspension was concentrated in vacuo
  3. customdried under vacuum

Sources & evidence

ORD record
ord-ee466bb698ba4af190b3f6e918b6770e
Source dataset
uspto-grants-2013_03
Patent number
US08404837B2

Reaction notes

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