Hydrogen Bromide → HCID 68131887, compound

HRID 268290Notes

Reaction equation

HRID 268290 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19]C)=[CH:16][CH:17]=3)[CH2:12][N:11]([CH3:21])[CH2:10]2)=[CH:5][CH:4]=1.[BrH:22]>>[BrH:22].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=3)[CH2:12][N:11]([CH3:21])[CH2:10]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 68134002HCID 68134002, compound

Product 1

HCID 68131887HCID 68131887, compound

Procedure

The free base prepared from 12.2 g. of rac.-4-(4-chlorophenyl)-1,2,3,4-tetrahydro-7-methoxy-2-methylisoquinoline hydrochloride is stirred at reflux with 150 ml. of 48% hydrobromic acid solution for 2 hours at a bath temperature of 160°. After evaporation and recrystallization from methanol-ether there is obtained rac.-4-(4-chlorophenyl)-1,2,3,4-tetrahydro-2-methyl-7-isoquinolinol hydrobromide of m.p. 292°-293°. The free base of this compound displays a m.p. of 189°-190° after recrystallization from ether, the hydrochloride after recrystallization from methanol-ether melts at 295°-297°.

Workup

  1. customThe free base prepared from 12.2 g
  2. temperatureat reflux with 150 ml
  3. customAfter evaporation and recrystallization from methanol-ether

Sources & evidence

ORD record
ord-89869ac139b74ce5b500d5edf99beae8
Source dataset
uspto-grants-1976_03
Patent number
US03947456

Reaction notes

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