Water → N,N-dimethyl-5-nitropyridin-2-amine

HRID 1925393Notes

Reaction equation

HRID 1925393 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Cl.[CH3:12][NH:13][CH3:14].C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH3:12][N:13]([CH3:14])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 783082-Chloro-5-nitropyridineHCID 81531Diisopropylethylamine

Product 1

HCID 75707N,N-dimethyl-5-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

2-Chloro-5-nitropyridine (3.57 g, 22.5 mmol), dimethylamine hydrochloride (5.50 g, 67.5 mmol) and diisopropylethylamine (13.7 mL, 78.7 mmol) were combined in DMSO (15 mL) and the reaction mixture was heated at 80° C. for 4 h. After cooling to RT, water was added and the desired N,N-dimethyl-5-nitropyridin-2-amine was isolated by filtration and used in the next step without further purification.

Workup

  1. temperatureAfter cooling to RT

Sources & evidence

ORD record
ord-da03610e674b4bfe897afbabd2297416
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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