Hydrogen Bromide → HCID 22406801, compound

HRID 440485Notes

Reaction equation

HRID 440485 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([F:23])=[C:18]([O:21]C)[CH:19]=3)[CH2:14][CH2:13][N:12]2[CH3:24])[CH2:10][CH2:9]1.[BrH:25]>C(O)(=O)C>[BrH:25].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([F:23])=[C:18]([OH:21])[CH:19]=3)[CH2:14][CH2:13][N:12]2[CH3:24])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 22406729HCID 22406729, compound

Product 1

HCID 22406801HCID 22406801, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-[1-(2-chlorophenyl)cyclopropyl]-6-fluoro-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (18.0 g) in acetic acid (150 ml) and 48% aqueous hydrobromic acid (150 ml) was heated under reflux under argon for 220 minutes. The solvent was removed in vacuo, and the residue dried by azeotropic distillation with propan-2-ol and crystallised from propan-2-ol to yield 1-[1-(2-chlorophenyl)cyclopropyl]-6-fluoro-7-hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (18.56 g), m.p. 240° C. (dec).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under argon for 220 minutes
  3. customThe solvent was removed in vacuo
  4. dry with materialthe residue dried by azeotropic distillation with propan-2-ol
  5. customcrystallised from propan-2-ol

Sources & evidence

ORD record
ord-bbe5735b48504c77b58228a65ea6e860
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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