2,3-Dimethylquinoline → 8-(Bromomethyl)-7-chloro-3-methylquinoline

HRID 231211Notes

Reaction equation

HRID 231211 reaction equation
[Cl:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[C:7]([CH3:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:19]Br.CC1C(C)=NC2C(C=1)=CC=CC=2>ClC1C=CC=CC=1Cl.O>[Br:19][CH2:12][C:11]1[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][C:7]([CH3:13])=[CH:6]2

Participants

7

Reactant 4

HCID 155912,3-DimethylquinolineHCID 24408BromineHCID 517045Sodium AcetateHCID 133097887-Chloro-3,8-dimethylquinoline

Product 1

HCID 133097898-(Bromomethyl)-7-chloro-3-methylquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

9.6 g of 7-chloro-3,8-dimethylquinoline are dissolved in 850 g of 1,2-dichlorobenzene, 6.2 g of sodium acetate, dissolved in 150 ml of water, and then 8 g of bromine are added, and the mixture is exposed to a 150 watt low pressure mercury lamp for from 5 to 6 hours at 15° C. The yield, determined chromatographically, is 80% of theory, based on converted dimethylquinoline. The selectivity of the reaction is 88% at a conversion of 91%. Table 1 sumarizes the result of varying the reaction conditions.

Workup

  1. customis exposed to a 150 watt low pressure mercury lamp for from 5 to 6 hours at 15° C
  2. customresult
  3. customthe reaction conditions

Sources & evidence

ORD record
ord-41b3b62f833a4b2fb80e5ce6d2342d15
Source dataset
uspto-grants-1989_07
Patent number
US04845226

Reaction notes

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