Dichloromethane → N-(2-aminoethyl)-3-bromopyridine-2-carboxamide hydrochloride

HRID 34936Notes

Reaction equation

HRID 34936 reaction equation
[Br:1][C:2]1[C:3]([C:8]([NH:10][CH2:11][CH2:12][NH:13]C(=O)OC(C)(C)C)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.C(Cl)[Cl:29]>>[ClH:29].[NH2:13][CH2:12][CH2:11][NH:10][C:8]([C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:9]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 13800219HCID 13800219, compound

Product 1

HCID 13800246N-(2-aminoethyl)-3-bromopyridine-2-carboxamide hydrochloride

Procedure

3.2 g of t-butyl [2-(3-bromopyridine-2-carboxamido)ethyl]carbamate were heated to reflux for 4 hours with 3.5 ml of methylene chloride and 3.5 ml of trifluoroacetic acid. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethanol and the solution was treated with an equimolar amount of ethanolic hydrochloric acid. The hydrochloride was recrystallized from methanol/ether, whereby there was obtained N-(2-aminoethyl)-3-bromopyridine-2-carboxamide hydrochloride as white crystals, m.p. 279°.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol
  3. additionthe solution was treated with an equimolar amount of ethanolic hydrochloric acid
  4. customThe hydrochloride was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-041fa8d9cec1462ca5db313f84321533
Source dataset
uspto-grants-1988_08
Patent number
US04764522

Reaction notes

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