Hydrogen Bromide → HCID 68132294, compound

HRID 268292Notes

Reaction equation

HRID 268292 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1.Br>>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 68132626HCID 68132626, compound

Product 1

HCID 68132294HCID 68132294, compound

Procedure

The free base isolated from 4.00 g. of rac.-4-(3-chlorophenyl)-1,2,3,4-tetrahydro-7-methoxy-2-methylisoquinoline hydrochloride is heated for an hour at 150° (bath temperature) with 80 ml. of 48% hydrobromic acid. After concentration, it is extracted with ethyl acetate and sodium bicarbonate solution. By acidification of the ethyl acetate extract with ethanolic hydrogen chloride and by crystallization and recrystallization from methanol-ether there is obtained rac.-4-(3-chlorophenyl)-1,2,3,4-tetrahydro-2-methyl-7-isoquinolinol hydrochloride, m.p. 258°-259°. The base released therefrom displays a m.p. of 196°-197° after recrystallization from ether-petroleum ether.

Workup

  1. customThe free base isolated from 4.00 g
  2. concentrationAfter concentration, it
  3. extractionis extracted with ethyl acetate and sodium bicarbonate solution
  4. extractionBy acidification of the ethyl acetate extract with ethanolic hydrogen chloride and by crystallization and recrystallization from methanol-ether

Sources & evidence

ORD record
ord-bff29e9416e0461da338360b28e7608e
Source dataset
uspto-grants-1976_03
Patent number
US03947456

Reaction notes

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