Hydrogen Bromide → HCID 14848601, compound

HRID 467314Notes

Reaction equation

HRID 467314 reaction equation
Cl.[CH2:2]([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:20]C)=[CH:15][CH:16]=2)[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BrH:22]>C(O)(=O)C>[BrH:22].[CH2:2]([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([OH:20])=[CH:15][CH:16]=2)[CH2:11]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen Bromide2×HCID 14750911HCID 14750911, compound

Product 1

HCID 14848601HCID 14848601, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 25 g of 2-benzylamino-7-methoxytetraline hydrochloride, PREPARATION I (a), in 215 ml of a 33% hydrobromic acid solution in acetic acid and in the presence of 36 ml of 48% hydrobromic acid, is heated at reflux for 2 hours under stirring. After concentration under reduced pressure, the residue is taken up three times with 100 ml of absolute ethanol and dried every time. The product thus obtained is triturated with 150 ml of acetone, the mixture is filtered to give 25.3 g of 2-benzylamino-7-hydroxytetraline hydrobromide; m.p. 198°-200° C. The salt is dissolved in 1300 ml of hot water and, after cooling, there is added a concentrated ammonium hydroxide solution. The base is extracted with ethyl acetate, dried and a solid is obtained which after crystallization from 250 ml of toluene gives 14 g of 2-benzylamino-7-hydroxytetraline base; m.p. 161°-163° C.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationAfter concentration under reduced pressure
  3. customdried every time
  4. customThe product thus obtained
  5. customis triturated with 150 ml of acetone
  6. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-de197e33c7e24dd289494a36eecebf12
Source dataset
uspto-grants-1992_10
Patent number
US05159103

Reaction notes

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