Hydrochloric Acid → 5-(Aminomethyl)-2-chloropyridine

HRID 1467369Notes

Reaction equation

HRID 1467369 reaction equation
Cl.C1(C)C=CC=CC=1.C=[N:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[N:16][CH:17]=1>O>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][NH2:10])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 20694807HCID 20694807, compound

Product 1

HCID 70209275-(Aminomethyl)-2-chloropyridineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

On the other hand, 7 g of concentrated hydrochloric acid was added to the toluene layer, and the resulting water layer containing the hydrochloride salt of an N-methylidene-(2-chloro-pyridin-5-yl)methylamine oligomer (II-5) or a mixture of two or more such salts was separated. 3.2 g of methanol was added to the separated water layer, and the resulting mixture was treated for 3 hours at 60° C., yielding an aqueous solution of the hydrochloride salt of (2-chloropyridin-5-yl)methylamine. Analysis by HPLC revealed an amount of the (2-chloropyridin-5-yl)methylamine of 1.28 g (yield: 90%).

Workup

  1. additiona mixture of two or more such salts
  2. customwas separated
  3. addition3.2 g of methanol was added to the separated water layer
  4. additionthe resulting mixture was treated for 3 hours at 60° C.

Sources & evidence

ORD record
ord-bb4b70411b054ff78925f937623ab6a5
Source dataset
uspto-grants-2015_04
Patent number
US09000156B2

Reaction notes

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