N-Methylaniline → HCID 12031822, compound

HRID 418680Notes

Reaction equation

HRID 418680 reaction equation
[C:1]1([C:7]([OH:9])=[O:8])([C:4](O)=[O:5])[CH2:3][CH2:2]1.[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1.CCOC(C)=O>[CH3:10][N:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([C:1]1([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)=[O:5]

Participants

5

Reactant 2

HCID 7515N-MethylanilineHCID 690171,1-Cyclopropanedicarboxylic acid

Product 1

HCID 12031822HCID 12031822, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cyclopropane-1,1-dicarboxylic acid (1.5 g, 11.53 mmol) in THF (24 mL) TEA (1.6 mL, 11.53 mmol) was added dropwise and under stirring thionyl chloride (0.83 mL, 11.53 mmol) and the mixture stirred 30 min at room temperature. A solution of N-methylaniline (1.3 mL, 11.53 mmol) in THF (14 mL) was added dropwise at 0° C. and the mixture was stirred for 2 h. The mixture was diluted with EtOAc, extracted with 2N NaOH, acidified to pH˜2 by addition of 2N HCl and extracted with EtOAc, dried over anhydrous Na2SO4 and concentrated under reduced pressure affording 246 (1.24 g, 5.66 mmol, 49%) as a white solid. MS (m/z): (M+1) 220.0 (100%).

Workup

  1. stirringthe mixture was stirred for 2 h
  2. extractionextracted with 2N NaOH
  3. additionacidified to pH˜2 by addition of 2N HCl
  4. extractionextracted with EtOAc
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e9ade49973e4229b1629b462f5001b7
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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