Hydrochloric Acid → 1-(3,4,5-Trimethoxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 543733Notes

Reaction equation

HRID 543733 reaction equation
[ClH:1].C(OC([N:12]([CH2:25][CH:26]1[C:35]2[C:30](=[CH:31][C:32]([OH:37])=[C:33]([OH:36])[CH:34]=2)[CH2:29][CH2:28][NH:27]1)[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=1)=O)C1C=CC=CC=1.Cl>C(O)(=O)C>[ClH:1].[CH3:24][O:23][C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([O:19][CH3:20])[C:16]=1[O:21][CH3:22])[NH:12][CH2:25][CH:26]1[C:35]2[C:30](=[CH:31][C:32]([OH:37])=[C:33]([OH:36])[CH:34]=2)[CH2:29][CH2:28][NH:27]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 204605511-(N-benzyloxycarbonyl-3,4,5-trimethoxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 204605191-(3,4,5-Trimethoxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 69.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(N-benzyloxycarbonyl-3,4,5-trimethoxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (4.4 g), conc. hydrochloric acid (45 ml) and acetic acid (45 ml) was refluxed for 1.5 hours in a stream of nitrogen. The reaction mixture was concentrated to dryness and the residue was washed with ether and acetone and crystallized with methanol to give 1-(3,4,5-trimethoxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.3 g). The product was recrystallized from water to give a pure product, mp 223° to 225° C.

Workup

  1. temperaturewas refluxed for 1.5 hours in a stream of nitrogen
  2. concentrationThe reaction mixture was concentrated to dryness
  3. washthe residue was washed with ether and acetone
  4. customcrystallized with methanol

Sources & evidence

ORD record
ord-e83c280231ca440daa8d9afa6363fb52
Source dataset
uspto-grants-1984_05
Patent number
US04447436

Reaction notes

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