Water → 2-trifluoromethyl-nicotinic acid N'-(3,4-dimethoxy-5-nitro-benzoyl)-hydrazide

HRID 1920062Notes

Reaction equation

HRID 1920062 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.[F:17][C:18]([F:30])([F:29])[C:19]1[N:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([NH:23][NH2:24])=[O:22].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:6]([NH:24][NH:23][C:21](=[O:22])[C:20]1[CH:25]=[CH:26][CH:27]=[N:28][C:19]=1[C:18]([F:17])([F:29])[F:30])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 219286243,4-Dimethoxy-5-nitrobenzoic acidHCID 670371942-(Trifluoromethyl)pyridine-3-carbohydrazide

Product 1

HCID 670371772-trifluoromethyl-nicotinic acid N'-(3,4-dimethoxy-5-nitro-benzoyl)-hydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,4-dimethoxy-5-nitrobenzoic acid (0.53 g, 2.34 mmol) and 1,1-carbonyldiimidazole (0.42 g, 2.59 mmol) was heated in tetrahydrofuran (10 mL) at reflux for three hours and then cooled to room temperature. 2-Trifluoromethyl-nicotinic acid hydrazide (0.53 g, 2.57 mmol) was added in one portion and the yellowish mixture was stirred at reflux overnight and then allowed to cool to room temperature. The mixture was poured onto cold water (100 mL) and the copious precipitate was filtered off, washed with water and dried to give 2-trifluoromethyl-nicotinic acid N′-(3,4-dimethoxy-5-nitro-benzoyl)-hydrazide, 0.71 g (73%).

Workup

  1. temperatureat reflux for three hours
  2. temperatureat reflux overnight
  3. temperatureto cool to room temperature
  4. filtrationthe copious precipitate was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-34e15dbf768e4e38bfaa7abdb369acf7
Source dataset
uspto-grants-2012_05
Patent number
US08168793B2

Reaction notes

Loading…