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

HRID 27161Notes

Reaction equation

HRID 27161 reaction equation
[ClH:1].C(OC([N:12]([CH2:20][CH:21]1[C:30]2[C:25](=[CH:26][C:27]([OH:32])=[C:28]([OH:31])[CH:29]=2)[CH2:24][CH2:23][NH:22]1)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=O)C1C=CC=CC=1.Cl>C(O)(=O)C>[ClH:1].[F:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[NH:12][CH2:20][CH:21]1[C:30]2[C:25](=[CH:26][C:27]([OH:32])=[C:28]([OH:31])[CH:29]=2)[CH2:24][CH2:23][NH:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 204605491-(N-benzyloxycarbonyl-m-fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 204605161-(m-Fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 94.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1(N-benzyloxycarbonyl-m-fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.3 g), conc. hydrochloric acid (3 ml) and acetic acid (3 ml) was refluxed for 1.5 hours in a stream of nitrogen. The reaction mixture was concentrated and the residue was pulverized with ether to give 1-(m-fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.2 g), powder.

Workup

  1. temperaturewas refluxed for 1.5 hours in a stream of nitrogen
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-70d76efda4c841af9020f38055308666
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Reaction notes

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