Phthalaldehydic acid → 2-Formyl-N,N-dimethylbenzamide

HRID 1040398Notes

Reaction equation

HRID 1040398 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6])=[O:2].[CH:12]([N:15](CC)[CH:16](C)C)(C)C.CNC.C(O)C>ClCCl.C(OCC)C>[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([N:15]([CH3:16])[CH3:12])=[O:6])=[O:2]

Participants

6

Reactant 3

HCID 8406Phthalaldehydic acidHCID 81531DiisopropylethylamineHCID 22184060Dimethylamine ethanol

Product 1

HCID 154454632-Formyl-N,N-dimethylbenzamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-formylbenzoic acid (500 mg, 3.33 mmol), N,N-diisopropylethylamine (0.58 mL, 3.3 mmol), and dimethylamine/ethanol solution (1.2 mL, 5.6 M, 6.7 mmol) in 3.3 mL of dichloromethane was added 1-ethyl-3-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride (1.28 g, 6.67 mmol) at 0° C. After being stirred at room temperature overnight, the reaction mixture was diluted with diethyl ether. The solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo to obtain the title compound as a slightly yellow oil (113 mg, 19%).

Workup

  1. washThe solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9048f96c758b4c56967335ca56e32ee4
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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