Hydrogen Bromide → 4-Hydroxybenzylamine

HRID 2164908Notes

Reaction equation

HRID 2164908 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.Br>I>[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 754524-Methoxybenzylamine

Product 1

HCID 974724-HydroxybenzylamineYield 130.9%

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Procedure

10 g 4-methoxy benzylamine chlorohydrate of formula (IV) are reflux boiled for 4 hours with 16 ml hydrobromic acid 48% (d=1.47) (or 20 ml aqueous hydroiodic acid). The obtained solution is vacuum concentrated to dryness. The residue, treated with acetonitrile, provides 11.75 g (theorical yield, m.p. 175°-180° C.) 4-hydroxy benzylamine bromohydrate of formula (V) when HBr is used.

Workup

  1. concentrationconcentrated to dryness
  2. additionThe residue, treated with acetonitrile

Sources & evidence

ORD record
ord-2d49324ed4e14b12a503774f308ee664
Source dataset
uspto-grants-1985_03
Patent number
US04507499

Reaction notes

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