Dichloromethane → N-(2-aminoethyl)-4-nitropyridine-2-carboxamide hydrochloride

HRID 34935Notes

Reaction equation

HRID 34935 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([NH:12][CH2:13][CH2:14][NH:15]C(=O)OC(C)(C)C)=[O:11])[CH:5]=1)([O-:3])=[O:2].FC(F)(F)C(O)=O.C(Cl)[Cl:31]>>[ClH:31].[NH2:15][CH2:14][CH2:13][NH:12][C:10]([C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][N:7]=1)=[O:11]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 13800214t-Butyl [2-(4-nitropyridine-2-carboxamido)ethyl]carbamate

Product 1

HCID 13800216N-(2-aminoethyl)-4-nitropyridine-2-carboxamide hydrochloride

Procedure

7.0 g of t-butyl [2-(4-nitropyridine-2-carboxamido)ethyl]carbamate were stirred at room temperature with 9 ml of methylene chloride and 9 ml of trifluoroacetic acid. Thereafter, the reaction mixture was concentrated under reduced pressure. The residue was converted with hydrogen chloride in ethanol into the hydrochloride and this was recrystallized from ethanol/ether. There was obtained N-(2-aminoethyl)-4-nitropyridine-2-carboxamide hydrochloride as white crystals, m.p. 193°-194°.

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  2. customthis was recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-15105d9027ba4f81884ec22632f6943d
Source dataset
uspto-grants-1988_08
Patent number
US04764522

Reaction notes

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