Hydrogen Bromide → 8-Chloro-7-hydroxy-4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide

HRID 1089809Notes

Reaction equation

HRID 1089809 reaction equation
[Cl:1][C:2]1[C:3]([O:22]C)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][NH:9][CH2:8][CH:7]2[C:12]1[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([O:20]C)[CH:13]=1.[BrH:24]>>[BrH:24].[Cl:1][C:2]1[C:3]([OH:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][NH:9][CH2:8][CH:7]2[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([OH:20])[CH:13]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 106166778-Chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 147195718-Chloro-7-hydroxy-4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide

Procedure

To 540 mg of 8-chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline was added 11 ml of 48% hydrobromic acid, and the mixture was heated under reflux for 3 hours under an argon gas stream. After cooling, the crystals which separated out were collected by filtration and 520 mg of 8-chloro-7-hydroxy-4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours under an argon gas stream
  3. temperatureAfter cooling
  4. customthe crystals which separated out
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-1e62a969f4fc42deb95426da9dc17cb8
Source dataset
uspto-grants-1992_01
Patent number
US05079256

Reaction notes

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