Thionyl Chloride → 3-(Chloromethyl)isoquinoline hydrochloride

HRID 443812

Reaction equation

HRID 443812 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.S(Cl)([Cl:15])=O>>[ClH:15].[Cl:15][CH2:2][C:3]1[N:4]=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12874869Isoquinolin-3-ylmethanol

Product 1

HCID 128748713-(Chloromethyl)isoquinoline hydrochloride

Conditions

Temperature
5 °C

Procedure

3-Hydroxymethylisoquinoline (110 g) is added to thionyl chloride (130 cc), whilst cooling so as to keep the temperature between 25° and 30° C. The reaction mixture is then heated to the reflux temperature at a rate which is such that the evolution of gas is not excessive. The mixture is heated under reflux for 90 minutes (until the evolution of gas ceases), and then for a further 30 minutes. It is then cooled to 5° C. with ice, the slurry formed is filtered and the solid is washed with diethyl ether. 3-Chloromethylisoquinoline hydrochloride (136 g), melting at 202° C., is obtained.

Workup

  1. temperaturewhilst cooling so as
  2. customthe temperature between 25° and 30° C
  3. temperatureThe reaction mixture is then heated to the reflux temperature at a rate which
  4. temperatureThe mixture is heated
  5. temperatureunder reflux for 90 minutes (until the evolution of gas ceases), and then for a further 30 minutes
  6. customthe slurry formed
  7. filtrationis filtered
  8. washthe solid is washed with diethyl ether

Sources & evidence

ORD record
ord-fd911da2821140ef80f91ad7a78d59d9
Source dataset
uspto-grants-1981_04
Patent number
US04261993

Linked notes

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