N-methyl-2-pyrrolidone → 2-(3-Methyl-5-(2-nitrophenyl)-4H-1,2,4-triazol-4-yl)benzoic acid

HRID 722206

Reaction equation

HRID 722206 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([NH:8][NH2:9])=O)([O-:3])=[O:2].[CH3:14][C:15]1[O:16][C:17](=[O:25])[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.CN1CCCC1=O>O>[CH3:14][C:15]1[N:20]([C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[C:17]([OH:25])=[O:16])[C:6]([C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])=[N:8][N:9]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 68236AcetanthranilHCID 3781218o-Nitrobenzohydrazide

Product 1

HCID 218838872-(3-Methyl-5-(2-nitrophenyl)-4H-1,2,4-triazol-4-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The mixture consisting of 1.8 g of 2-nitrobenzoic hydrazide, 1.6 g of 2-methylbenzo[d][1,3]oxazin-4-one and 5 ml of N-methylpyrrolidone was heated to 80° C. with stirring for 2 hours. After cooling, the mixture was admixed with water to slight cloudiness and stirred for a further 1 hour, during which time a solid precipitated out which was filtered off with suction, recrystallized from ethanol and dried under reduced pressure.

Workup

  1. temperatureAfter cooling
  2. stirringstirred for a further 1 hour, during which time a solid
  3. customprecipitated out which
  4. filtrationwas filtered off with suction
  5. customrecrystallized from ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-2e1c1b592807413fad6a2171d1fcfa5d
Source dataset
uspto-grants-2006_11
Patent number
US07138414B2

Linked notes

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