4-Pyridinecarboxaldehyde → HCID 87352693, compound

HRID 1011975Notes

Reaction equation

HRID 1011975 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.C([O-])(=O)C.[Na+].[N:18]1[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=1.[OH-].[NH4+]>C(O)(=O)C>[N:18]1[CH:23]=[CH:22][C:21](/[CH:24]=[N:10]/[NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 133894-PyridinecarboxaldehydeHCID 14923Ammonium HydroxideHCID 98650(3-(Trifluoromethyl)phenyl)hydrazineHCID 517045Sodium Acetate

Product 1

HCID 87352693HCID 87352693, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-(Trifluoromethyl)phenylhydrazine (176 mg, 1 mmol) in 5 ml of acetic acid were treated with sodium acetate (164 mg, 2 mmol) and pyridine-4-carbaldehyde (0.11 ml, 1 mmol) during 1 h at 50° C. The yellow solution was cooled and ammonium hydroxide 25% was added, the solid was collected, washed with water and recrystallized from EtOAc:n-heptane. The title compound was obtained as a yellow solid (195 mg, 74%). MS: 266.1 (MH+).

Workup

  1. temperatureThe yellow solution was cooled
  2. customthe solid was collected
  3. washwashed with water
  4. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-5a0f5e45ee8c49b284cbfcbd528ca14f
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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