Methanol → N-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]pyridine-2-carboxamide

HRID 1022844Notes

Reaction equation

HRID 1022844 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[C:16]([CH3:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][NH:34][NH2:35].C[OH:37]>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:25])([F:24])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17](/[CH:18]=[N:35]/[NH:34][C:33]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=4)=[O:37])=[C:16]([CH3:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 162287212-(Hydrazinylmethyl)pyridineHCID 866585204-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde

Product 1

HCID 87403792N-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]pyridine-2-carboxamideYield 45%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

A solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde (i.e. the product of Step 1, 500 mg), concentrated hydrochloric acid (5 drops) and 2-picolyl hydrazine (188 mg) in methanol (20 mL) were heated at reflux for 5 h. The mixture was concentrated and the residue was triturated with water. Filtration yielded the title compound (289 mg, 45%).

Workup

  1. temperatureat reflux for 5 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was triturated with water
  4. filtrationFiltration

Sources & evidence

ORD record
ord-8f3bf04ac2834754bd5e7b46229df120
Source dataset
uspto-grants-2014_05
Patent number
US08722673B2

Reaction notes

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