Hydrogen Bromide → 2-Amino-5-methylpyridine

HRID 1995748Notes

Reaction equation

HRID 1995748 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

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 87810Pyridine, hydrobromide (1:1)HCID 20487965HCID 20487965, compound

Product 2

HCID 153482-Amino-5-methylpyridineHCID 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.

Workup

  1. customwas held at 165° C

Sources & evidence

ORD record
ord-9f1ce4bf223f43c9a437ef77c4f84f22
Source dataset
uspto-grants-1983_09
Patent number
US04405790

Reaction notes

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