Pyridine → HCID 2933534, compound

HRID 230801Notes

Reaction equation

HRID 230801 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=1>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 778882-Amino-5-nitropyridine

Product 1

HCID 2933534HCID 2933534, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

P-toluenesulfonyl chloride (143.9 g) was added to a pyridine solution (800 mL) of 2-amino-5-nitropyridine (100 g), and stirred overnight at 110° C. The reaction solution was poured into water with ice, and stirred at 15° C. or lower for 30 minutes. The precipitate was taken out through filtration, and the resulting residue was washed with water, diethyl ether (1500 mL) and ethyl acetate (1000 mL), and dried under reduced pressure to obtain the entitled compound (176.8 g).

Workup

  1. stirringstirred at 15° C. or lower for 30 minutes
  2. filtrationThe precipitate was taken out through filtration
  3. washthe resulting residue was washed with water, diethyl ether (1500 mL) and ethyl acetate (1000 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-8022163897b3450b8dc4c8bb564958e7
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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