Pyrrolidine → HCID 12152140, compound

HRID 658974Notes

Reaction equation

HRID 658974 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C>CS(C)=O.C(O)(C)C>[N+:8]([C:7]1[C:2]([NH2:1])=[N:3][C:4]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 12152140HCID 12152140, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
60 °C

Procedure

A suspension of 1.735 g (10 mmol) of 2-amino-6-chloro-3-nitropyridine, 1.66 ml (20 mmol) of pyrrolidine and 1.66 ml (10 mmol) of diisopropylethylamine in a mixture of 1 ml of dimethyl sulfoxide and 5 ml of isopropanol is heated at 60° C., with stirring, in a sealed tube, for 20 hours. The mixture is cooled to ambient temperature and then diluted with 10 ml of isopropanol. The solid is collected by filtration and is then washed with 2×5 ml of isopropanol. The solid is taken up with 20 ml of water. The suspension is stirred for 30 minutes. The solid is filtered off and then washed with 2×5 ml of water and 2×5 ml of ether, and dried under vacuum in the presence of phosphorus pentoxide so as to obtain 1.91 g (9.17 mmol) of product in the form of a vivid yellow powder.

Workup

  1. temperatureThe mixture is cooled to ambient temperature
  2. filtrationThe solid is collected by filtration
  3. washis then washed with 2×5 ml of isopropanol
  4. stirringThe suspension is stirred for 30 minutes
  5. filtrationThe solid is filtered off
  6. washwashed with 2×5 ml of water and 2×5 ml of ether
  7. dry with materialdried under vacuum in the presence of phosphorus pentoxide so as

Sources & evidence

ORD record
ord-1108b535e79d4ecd9cef007491fefaae
Source dataset
uspto-grants-2011_12
Patent number
US08080547B2

Reaction notes

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