Hydrochloric Acid → 5-chloroisoquinoline

HRID 1447115Notes

Reaction equation

HRID 1447115 reaction equation
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[ClH:12].N([O-])=O.[Na+]>>[Cl:12][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 707665-AminoisoquinolineHCID 23668193Sodium Nitrite

Product 1

HCID 2249335-chloroisoquinoline

Procedure

5-Aminoisoquinoline is reacted with hydrochloric acid, sodium nitrite and cuprous chloride to afford 5-chloroisoquinoline, which was then reduced with diborane in tetrahydrofuran. The resultant 5-chlorotetrahydroisoquinoline was then acetylated with acetic anhydride and chlorosulfonated with chlorosulfonic acid at low temperature, for example -50° C., to afford the desired chlorosulfonyl tetrahydroisoquinoline.

Sources & evidence

ORD record
ord-5ca2cec3b9f6445db80b4640ccee6356
Source dataset
uspto-grants-1982_02
Patent number
US04315935

Reaction notes

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