Bromine → Sulfuric Acid

HRID 1381014Notes

Reaction equation

HRID 1381014 reaction equation
BrBr.[S:3]([OH:7])([OH:6])(=[O:5])=[O:4].[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=1>OS(O)(=O)=O.O=S(=O)=O>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=1.[S:3](=[O:5])(=[O:4])([OH:7])[OH:6]

Participants

5

Reactant 2

HCID 24408BromineHCID 704229932-(4-Aminobutyl)-3-methylpyridine sulphate

Product 2

HCID 1118Sulfuric AcidHCID 201959674-(3-Methylpyridin-2-YL)butan-1-amine

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent

Procedure

Bromine (10 g) was added dropwise with stirring to a solution of 2-(4-aminobutyl)-3-methylpyridine sulphate (21.3 g) obtained from 2-(4-aminobutyl)-3-methylpyridine and concentrated sulphuric acid) in 65% oleum (100 ml) at room temperature. The solution was then heated to 55° C. and stirred overnight. The solution was cooled and added slowly to ice (38 g). The resultant solution was poured into water (250 ml) and taken to pH 2.5 with aqueous ammonia solution (s.g. 0.88) and a dibrominated impurity crystallized which was removed by filtration. The filtrate was taken to pH 9.5 and extracted with dichloromethane and the extracts were dried (MgSO4) and decolourised with charcoal.

Sources & evidence

ORD record
ord-50f9fc9cde4b434cada89669f847dbe9
Source dataset
uspto-grants-1986_04
Patent number
US04584381

Reaction notes

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