Pyridine → 3-Benzoylamino-5-nitro-2-pyridone

HRID 66362Notes

Reaction equation

HRID 66362 reaction equation
[NH2:1][C:2]1[C:3](=[O:11])[NH:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.N1C=CC=CC=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[C:18]([NH:1][C:2]1[C:3](=[O:11])[NH:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 227547823-Amino-5-nitropyridin-2(1H)-one

Product 1

HCID 227547673-Benzoylamino-5-nitro-2-pyridone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 100 mg. of 3-amino-5-nitro-2-pyridone in 1.5 ml. of pyridine was cooled and treated with 200 mg. of benzoyl chloride. After 2 hours water was added. The oil that separated was washed with water and triturated with ether. The resultant solid was recrystallized from ethyl acetate to give 3-benzoylamino-5-nitro-2-pyridone, m.p. 267°-268° C.

Workup

  1. additiontreated with 200 mg
  2. customThe oil that separated
  3. washwas washed with water
  4. customtriturated with ether
  5. customThe resultant solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c14a4005988345be85980af391aebba7
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Reaction notes

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