Hydrochloric Acid → HCID 15896351, compound

HRID 903564Notes

Reaction equation

HRID 903564 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[C:7](N)[CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].[ClH:15].N([O-])=O.[Na+].[S:20](=[O:22])=[O:21].[Cl-].[K+]>O.O1CCOCC1>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([S:20]([Cl:15])(=[O:22])=[O:21])[CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 4873Potassium ChlorideHCID 161000631-(8-Amino-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 15896351HCID 15896351, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution (1.9 gm., 0.01 m.) of N-acetyl-8-amino-1,2,3,4 tetrahydroisoquinoline in 10 ml. of concentrated hydrochloric acid is stirred and then cooled to 0° C. The solution is then diazotized by the addition of (0.9 gm., 0.013 m.) sodium nitrite dissolved in 6 ml. of water. The solution of the diazonium salt is added to a mixture of 9 ml. of dioxane saturated with sulfur dioxide containing (1.2 gm., 0.016 m.) potassium chloride and (0.9 gm., 0.004 m.) cupric chloride dihydrate. The mixture is stirred at 25° C. for one hour and then at 40°-60° C. for thirty minutes. The mixture is diluted with water, extracted with ethyl acetate and the solvent is evaporated to yield N-acetyl-8-chlorosulfonyl-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. dissolutiondissolved in 6 ml
  2. waitat 40°-60° C. for thirty minutes
  3. extractionextracted with ethyl acetate
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-fa233dca22c448c38d48a9cb111dd4a1
Source dataset
uspto-grants-1980_10
Patent number
US04228170

Reaction notes

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