Hydrogen Bromide → HCID 12773913, compound

HRID 1164545Notes

Reaction equation

HRID 1164545 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:20])=[C:15]([O:18]C)[CH:16]=3)[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[BrH:23]>C(O)(=O)C>[BrH:23].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:20])=[C:15]([OH:18])[CH:16]=3)[CH2:11][CH2:10][NH:9]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 260Hydrogen Bromide2×HCID 12821122HCID 12821122, compound

Product 1

HCID 12773913HCID 12773913, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-chlorophenoxy)methyl-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline (100 mg), 47% hydrobromic acid (3 ml) and acetic acid (1.5 ml) was heated at 100° C. in an oil bath for 4.5 hours, and to the mixture was further added 47% hydrobromic acid (0.5 ml), and the mixture was continuously heated for 0.5 hour. After the reaction, the solvent was distilled off under reduced pressure. The amorphous residue was dissolved in acetone, and to the solution was added ether, and the mixture was allowed to stand. The precipitated crystals were collected by filtration to give 1-(4-chlorophenoxy)methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (97 mg), mp 232° to 233° C. The product was identified with a sample by I.R. spectrum and N.M.R. spectrum.

Workup

  1. temperaturethe mixture was continuously heated for 0.5 hour
  2. customAfter the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe amorphous residue was dissolved in acetone
  5. additionto the solution was added ether
  6. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-7dba06b1b60048d7b5dc44b1b04ff340
Source dataset
uspto-grants-1983_01
Patent number
US04370332

Reaction notes

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