Pyridine → N-(5-nitro-1H-indazol-3-yl)benzamide

HRID 1452853Notes

Reaction equation

HRID 1452853 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[NH:13][N:12]=1.N1C=CC=CC=1>O>[N+:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[C:11]2[NH:10][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 31366553-Amino-5-nitroindazole

Product 1

HCID 22319544N-(5-nitro-1H-indazol-3-yl)benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(5-Nitro-1H-indazol-3-yl)benzamide can be obtained in the following way: 0.39 ml of benzoyl chloride is added dropwise to a solution, cooled to 0° C., of 0.6 g of 3-amino-5-nitro-1H-indazole and of 5 ml of pyridine. The medium is brought back to a temperature in the region of 20° C. and maintained with stirring for 18 hours. After addition of 20 ml of distilled water, the medium is extracted with 20 ml and 10 ml of ethyl acetate. The organic phases are pooled, dried over magnesium sulfate, filtered and concentrated by evaporation under reduced pressure. The residue thus obtained is purified by chromatography on a silica column with a dichloromethane/methanol (99/1 by volume) mixture as eluent. 0.9 g of N-(5-nitro-1H-indazol-3-yl)benzamide is thus obtained in the form of an orange solid melting at 231° C.

Workup

  1. customis brought back to a temperature in the region of 20° C.
  2. temperaturemaintained
  3. extractionthe medium is extracted with 20 ml and 10 ml of ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue thus obtained
  8. customis purified by chromatography on a silica column with a dichloromethane/methanol (99/1 by volume) mixture as eluent

Sources & evidence

ORD record
ord-139ea8c65de2442699d8f4af446ee7b3
Source dataset
uspto-grants-2009_01
Patent number
US07473701B2

Reaction notes

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