1,3-Dichloroisoquinoline → 1-t-Butoxy-3-chloroisoquinoline

HRID 1712218Notes

Reaction equation

HRID 1712218 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([Cl:18])[N:9]=1>C1(C)C=CC=CC=1>[C:2]([O:4][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([Cl:18])[N:9]=1)([CH3:5])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 2986251,3-DichloroisoquinolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 221415801-t-Butoxy-3-chloroisoquinolineYield 89.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Potassium tert-butoxide (2.2 g, 19.3 mmol) is added to a solution of 1,3-dichloroisoquinoline (3.2 g, 16.12 mmol) in toluene (40 mL). The solution is then heated at reflux, cooled to ambient temperature, and filtered through a silica pad. The filtrate is concentrated under reduced pressure and the residual yellow liquid is purified by distillation (210° C., 0.1 mm Hg), yielding 1-tert-butoxy-3-chloroisoquinoline (3.4 g, 89%).

Workup

  1. temperatureThe solution is then heated
  2. temperatureat reflux
  3. filtrationfiltered through a silica pad
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. distillationthe residual yellow liquid is purified by distillation (210° C., 0.1 mm Hg)

Sources & evidence

ORD record
ord-b2e90df4c28e446cbca31184ab1ceb0b
Source dataset
uspto-grants-2010_09
Patent number
US07790932B1

Reaction notes

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