Propylamine → HCID 22380280, compound

HRID 1594070Notes

Reaction equation

HRID 1594070 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([NH2:14])[CH2:12][CH3:13]>CCO>[N+:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[NH:14][CH2:11][CH2:12][CH3:13])([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 22380280HCID 22380280, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-3-nitro-pyridine (18.0 g, 114 mmol) in EtOH(300 ml) is added n-propylamine(46.9 ml, 568 mmol) slowly at 0° C. and the resulting yellow mixture is warmed to room temp. After stirring for 2 h, the reaction is concentrated in vacuo. The residue is purified by flash chromatography (eluent 50% Hex/EtOAc) to give (3-nitro-pyridin-4-yl)-propyl-amine as a yellow solid. 1H NMR (CDCl3) δ 9.16 (s, 1H), 8.25 (d, J=6 Hz, 1H), 8.15 (br s, 1H), 6.68 (d, J=6 Hz, 1H), 3.29 (q, J=6.8 Hz, 2H), 1.74 (sextet, J=7.2 Hz, 2H), 1.02 (t, J=7.6 Hz, 3H). LRMS calcd 181.19, found 182.5 (MH+).

Workup

  1. concentrationthe reaction is concentrated in vacuo
  2. customThe residue is purified by flash chromatography (eluent 50% Hex/EtOAc)

Sources & evidence

ORD record
ord-ce27dba8b2a340cdb8a815bf9af982f6
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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