Chlorosulfonic acid → 2-Acetyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride
Reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].[Cl:14][S:15](O)(=[O:17])=[O:16]>C(Cl)Cl>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([S:15]([Cl:14])(=[O:17])=[O:16])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
To a solution of 140 g. (0.8 mole) 2-acetyl-1,2,3,4-tetrahydroisoquinoline in 150 ml. dry methylene chloride at -15° C. with sufficient stirring was added dropwise 300 ml. (4.5 mole) chlorosulfonic acid. After the addition of the chlorosulfonic acid was complete, the reaction mixture was stirred for one hour at -15° C. and then heated to reflux for 2 hours. The reaction mixture was then cooled to 10° C. and then cautiously poured onto 3 l. of ice. The crude reaction product was then extracted in methylene chloride (2×150 ml.), dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to dryness at reduced pressure to afford 2-acetyl-7-chlorosulfonyl-1,2,3,4,-tetrahydroisoquinoline as a viscous yellow oil.
Workup
- additionwas added dropwise 300 ml
- temperatureheated
- temperatureto reflux for 2 hours
- temperatureThe reaction mixture was then cooled to 10° C.
- additioncautiously poured onto 3 l
- customThe crude reaction product
- extractionwas then extracted in methylene chloride (2×150 ml.)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated to dryness at reduced pressure
Sources & evidence
- ORD record
- ord-b1a23a2cc47c41488b566fee16559058
- Source dataset
- uspto-grants-1982_02
- Patent number
- US04315935
Reaction notes
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