Water → HCID 86587159, compound

HRID 2084262Notes

Reaction equation

HRID 2084262 reaction equation
[NH:1]([C:8]1[N:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([NH:12][NH2:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O.O>CCO>[F:18][C:19]([F:28])([F:29])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=[N:13][NH:12][C:10]([C:9]1[C:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:17][CH:16]=[CH:15][CH:14]=1)=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 679903-(Trifluoromethyl)benzaldehydeHCID 142651872-Anilinopyridine-3-carbohydrazide

Product 1

HCID 86587159HCID 86587159, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 2-anilino-nicotinic acid hydrazide (0.31 g, 1.05 mmol) in 20 mL EtOH was added 3-trifluoromethyl-benzaldehyde (0.182 g, 1.05 mmol) in 5 mL EtOH at room temperature. The mixture was refluxed for 4 h and cooled to room temperature, then diluted by 100 mL water. The precipitate was collected by filtration, washed with MeOH, and dried to yield the title compound (0.343 g, 85%). 1H NMR (acetone-d6): 11.40 (S, 1H), 11.80 (S, 1H), 8.56 (s, 1H), 8.37 (d, J=4.8 Hz, 1H), 8.22 (d, J=8.1 Hz, 1H), 8.13 (s, 1H), 8.06 (d, J=8.1 Hz, 1H), 7.80 (m, 3H), 7.12 (m, 1H), 7.32 (m, 2H), 7.0 (t, J=8.1 Hz, 1H), 6.86 (q, J=4.5 Hz, 1H).

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with MeOH
  4. customdried

Sources & evidence

ORD record
ord-65eafbe69bf441c4a20af29f6c091436
Source dataset
uspto-grants-2004_04
Patent number
US06716859B2

Reaction notes

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