Hydrochloric Acid → 1-(p-Chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride
Reaction equation
Cl.C(OC([N:12]([CH2:20][CH:21]1[C:30]2[C:25](=[CH:26][C:27]([O:39]CC3C=CC=CC=3)=[C:28]([O:31]CC3C=CC=CC=3)[CH:29]=2)[CH2:24][CH2:23][NH:22]1)[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=O)C1C=CC=CC=1.Cl>C(O)(=O)C>[ClH:19].[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([NH:12][CH2:20][CH:21]2[C:30]3[C:25](=[CH:26][C:27]([OH:39])=[C:28]([OH:31])[CH:29]=3)[CH2:24][CH2:23][NH:22]2)=[CH:18][CH:17]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 1-(N-benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dibenzyloxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.1 g), acetic acid (11 ml) and conc. hydrochloric acid (11 ml) was heated for 2 hours at 100° C. The reaction mixture was concentrated to dryness under reduced pressure and the residue was washed with ethyl acetate and ether and pulverized to give crude 1-(p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride. The product was converted into its p-toluenesulfonate and then again converted into its hydrochloride to give a pure product, mp 91° to 93° C. The product was identified by means of comparison with an authentic sample prepared by another process by its infrared absorption spectrum and nuclear magnetic resonance spectrum.
Workup
- concentrationThe reaction mixture was concentrated to dryness under reduced pressure
- washthe residue was washed with ethyl acetate and ether
Sources & evidence
- ORD record
- ord-8193c031823d40679dda68b2150f7fe4
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04220647
Reaction notes
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