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

HRID 1854692Notes

Reaction equation

HRID 1854692 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-dimethylbenzamideYield 19.3%

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 pale 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-011d504e93e1426bb6c9b1ea40993436
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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