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

HRID 27158Notes

Reaction equation

HRID 27158 reaction equation
Cl.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][C:16]([Cl:19])=[CH:15][CH:14]=1)=O)C1C=CC=CC=1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1>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:32])=[C:28]([OH:31])[CH:29]=3)[CH2:24][CH2:23][NH:22]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 6101p-Toluenesulfonic acidHCID 204605101-(N-benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 204605271-(p-Chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1(N-benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (5.1 g), conc. hydrochloric acid (51 ml) and acetic acid (51 ml) was refluxed for 3 hours. The reaction mixture was concentrated to dryness under reduced pressure and the residue was dissolved in water. The aqueous layer was washed with ethyl acetate, treated with activated charcoal and concentrated to dryness to give crude 1-(p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.8 g). The product was converted into its p-toluenesulfonate and then again converted into its hydrochloride by conventional techniques. The salt was recrystallized from water containing a small amount of hydrochloric acid to give pure 1-(p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride, mp 91° to 93° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. washThe aqueous layer was washed with ethyl acetate
  5. additiontreated with activated charcoal
  6. concentrationconcentrated to dryness
  7. customto give crude 1-(p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.8 g)
  8. customThe salt was recrystallized from water containing a small amount of hydrochloric acid

Sources & evidence

ORD record
ord-5458bbe14b444a24ba014a33499bdbec
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Reaction notes

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