Methyl 4-Formylbenzoate → HCID 90411589, compound

HRID 1503159Notes

Reaction equation

HRID 1503159 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.Cl.[F:14][C:15]([F:26])([F:25])[O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][CH:18]=1>CCO>[F:14][C:15]([F:25])([F:26])[O:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23]/[N:24]=[CH:1]/[C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochloride

Product 1

HCID 90411589HCID 90411589, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a magnetically stirred solution of methyl 4-formylbenzoate (1.71 g, 10.41 mmoL) dissolved in EtOH (mL) was added (4-(trifluoromethoxy)phenyl)-hydrazine hydrochloride (2 g, 10.41 mmoL) and the reaction was stirred at room temperature overnight. The solvent was concentrated under reduced pressure and dried under high vacuum to give (E)-methyl 4-((2-(4-(trifluoromethoxy)phenyl)-hydrazono)methyl)benzoate (3.08 g, 87%): mp 142-145° C.; 1H NMR (400 MHz, CDCl3) δ 10.10 (s, 1H), 8.04 (d, J=8.0 Hz, 2H), 7.72-7.65 (m, 3H), 7.13 (q, J=8.9 Hz, 4H), 3.93 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −58.36; ESIMS m/z 338 ([M+H])+.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-bb969796ad454dbb8232537d679f3170
Source dataset
uspto-grants-2015_12
Patent number
US09212150B2

Reaction notes

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