Hydrogen Bromide → 2-Amino-5-methylpyridine

Reaction equation

Br.Br.[CH2:3]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=1)[CH2:4][CH2:5][CH3:6].Br.N1C=CC=CC=1>>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=1.[CH2:3]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=1)[CH2:4][CH2:5][CH3:6]

Participants

Reactant 3

HCID 260Hydrogen Bromide2×

HCID 87810Pyridine, hydrobromide (1:1)

HCID 20487965HCID 20487965, compound

Product 2

HCID 153482-Amino-5-methylpyridine

HCID 13224294N-Butyl-5-methylpyridin-2-amine

Procedure

In the same equipment as described in Example 16, except that a peristaltic pump was used to control the rate of hydrobromic acid addition, a mixture of 1 mole of 2-butylamino-5-methylpyridine hydrobromide and 1 mole of pyridine hydrobromide was treated with hydrobromic acid in much the same manner as described in Example 16, except that the dealkylation temperature was held at 165° C. After 26.5 hours, there was obtained 0.79 mole of 2-amino-5-methylpyridine, 0.14 mole of 2-butylamino-5-methylpyridine and 0.75 mole of bromobutanes. Yield, based on recovered 2-butylamino-5-methylpyridine, 91.9%. There was also recovered 96% of the pyridine used in the dealkylation reaction.