1-Bromo-2-Chloroethane → HCID 67018656, compound

HRID 507008Notes

Reaction equation

HRID 507008 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:23])=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][Cl:33].[OH-].[Na+]>CN(C=O)C>[Cl:33][CH2:32][CH2:31][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:23])=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 67018640HCID 67018640, compound

Product 1

HCID 67018656HCID 67018656, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 3-(7-hydroxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid (570 mg), potassium carbonate (2.5 g) and 1-bromo-2-chloroethane (0.9 ml) in DMF (13 ml) and heated at 50° C. for 41 hours. The reaction mixture was cooled to 40° C. and 2N NaOH solution (8 ml) was added and the reaction mixture was stirred for 1.5 hours. The reaction mixture was allowed to cool and then adjusted to pH 1 using 1N HC1, the resulting solid was collected by filtration and washed with diethyl ether to yield 3-[7-(2-chloroethoxy)-4-methyl-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid as a brown solid (426 mg); NMR Spectrum: (DMSOd6) 1.14 (s, 3H), 2.27 (s, 3H), 4.01 (t, 2H), 4.41 (m, 2H), 7.14 (s, 1H), 7.50-7.57 (m, 2H), 7.73-7.78 (m, 3H), 7.96 (d, 1H), 13.05 (br s, 1H); Mass Spectrum: M+H+ 372.

Workup

  1. temperatureto cool
  2. filtrationthe resulting solid was collected by filtration
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-663abb98bb634fe8a1373b79c755b1cf
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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