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

HRID 1826248Notes

Reaction equation

HRID 1826248 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1.[CH3:13][C:14]([CH3:17])([O-:16])[CH3:15].[K+]>C1(C)C=CC=CC=1>[C:14]([O:16][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1)([CH3:17])([CH3:15])[CH3:13]

Participants

4

Reactant 2

HCID 2986251,3-DichloroisoquinolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 221415801-t-Butoxy-3-chloroisoquinolineYield 89.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

1.0 g (5.05 mmol) of 1,3-dichloroisoquinoline from example 16.2 was dissolved in 20 ml of dry toluene, admixed with 0.68 g (6.06 mmol) of potassium tert-butoxide and stirred at 80° C. for 3 h. After the mixture had been cooled, it was filtered together with 50 ml of dichloromethane through a short silica gel column (1×5 cm) and the solvent was removed under reduced pressure. 1.06 g (4.50 mmol, 89.1%) of 1-t-butoxy-3-chloroisoquinoline were obtained.

Workup

  1. temperatureAfter the mixture had been cooled
  2. filtrationit was filtered together with 50 ml of dichloromethane through a short silica gel column (1×5 cm)
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-19cd1ef559104d0f9b17b6a01242fd0e
Source dataset
uspto-grants-2006_05
Patent number
US07049473B2

Reaction notes

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