Phenylacetaldehyde → HCID 67209392, compound

HRID 402500Notes

Reaction equation

HRID 402500 reaction equation
[NH:1]([C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([O:13][CH3:14])[N:4]=1)[NH2:2].[C:15]1([CH2:21][CH:22]=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[CH3:14][O:13][C:5]1[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=[C:3]([NH:1][N:2]=[CH:22][CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:4]=1

Participants

4

Reactant 2

HCID 998PhenylacetaldehydeHCID 18185573HCID 18185573, compound

Product 1

HCID 67209392HCID 67209392, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-hydrazinyl-6-methoxy-4-(trifluoromethyl)pyridine [261360-23-0] (0.11 g, 0.55 mmol) and 2-phenylacetaldehyde (0.57 g, 0.66 mmol) in toluene (5 ml) was heated at reflux for 6 h using a Dean-Stark apparatus. The reaction mixture was concentrated under reduced pressure. The crude product was purified by flash column chromatography (5% EtOAc in hexane) to yield the title compound (0.11 g, 63%). [LCMS RtD=3.75 min; [M+H]+=310.1]

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe crude product was purified by flash column chromatography (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-aa51a9b7d9a141bfb79e916d94f69a2a
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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