Water → HCID 86683179, compound

HRID 1852075Notes

Reaction equation

HRID 1852075 reaction equation
C([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([Cl:15])=[N:7][CH:6]=1)C=C.CCO[C:19]([CH3:21])=O.O.[CH3:23]OCCOCCOC>[Cl-].[Na+].O>[CH2:23]([C:6]1[N:7]=[C:8]([Cl:15])[C:9]2[C:14]([C:5]=1[OH:4])=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:19]=[CH2:21]

Participants

6

Reactant 4

HCID 962Water2×HCID 8150DiglymeHCID 8857Ethyl Acetate2×HCID 86683178HCID 86683178, compound

Product 1

HCID 86683179HCID 86683179, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
180 °C

Procedure

4-(allyloxy)-1-chloroisoquinoline (1.0 g, 4.55 mmol) was dissolved in diglyme (5 mL) and heated to 180° C. for 1 h. The reaction was cooled down to rt before adding EtOAc and water. Washed EtOAc layer with water then brine solution. The organic layer was then dried and concentrated. The residue was purified by flash chromatography with 20% of EtOAc/hexane to afford 3-allyl-1-chloroisoquinolin-4-ol (670 mg, 67%) as product. MS: MS m/z 220.1 (M++1).

Workup

  1. temperatureThe reaction was cooled down to rt
  2. customThe organic layer was then dried
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography with 20% of EtOAc/hexane

Sources & evidence

ORD record
ord-20ee6d1a35884f8897038cbf1122f013
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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