2-Chloropropane → HCID 86683274, compound

HRID 1852264Notes

Reaction equation

HRID 1852264 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[C:5]([OH:13])=[CH:4][N:3]=1.[CH2:14]1CCN2C(=NCCC2)C[CH2:15]1.C(Cl)(C)C>>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[C:5]([O:13][CH2:14][CH3:15])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 63612-ChloropropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86683273HCID 86683273, compound

Product 1

HCID 86683274HCID 86683274, compoundYield 53.2%

Conditions

Temperature
120 °C

Procedure

To a solution of 1,5-dichloroisoquinoline-4-ol (0.5 g, 2.33 mmol) in DBU (1.06 g, 7.01 mmol) was added isopropyl chloride (0.27 g, 3.5 mmol) at room temperature. The reaction vessel (Pressure tube) was sealed and heated at 120° C. for 6 h. The reaction mass was quenched with 1.5 N HCl solution and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (0.3 g, 50.1%) as pale yellow solid.

Workup

  1. customThe reaction vessel (Pressure tube) was sealed
  2. customThe reaction mass was quenched with 1.5 N HCl solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customto get crude compound
  7. customThe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ad4fd08d68734e0097815e8e381bb666
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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