Acetone Cyanohydrin → Methyl 4-[(2-cyanopropan-2-yl)amino]benzoate

HRID 245012Notes

Reaction equation

HRID 245012 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.[CH3:12][C:13](O)([C:15]#[N:16])[CH3:14].S([O-])([O-])(=O)=O.[Na+].[Na+]>>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:13]([C:15]#[N:16])([CH3:14])[CH3:12])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 6406Acetone CyanohydrinHCID 12082Methyl 4-aminobenzoateHCID 24436Sodium Sulfate

Product 1

HCID 13639520Methyl 4-[(2-cyanopropan-2-yl)amino]benzoateYield 92%

Procedure

A mixture of 4-aminobenzoic acid methyl ester (0.32 g, 2.12 mmol), acetonecyanohydrin (3 ml) and sodium sulfate (1 g) was refluxed for 15 hours. After filtration to remove the sodium sulfate, the filtrate was washed with brine and extracted with ethyl acetate. The organic layer was concentrated and chromatographed (dichloromethane:acetone, 60:40) to yield 4-[(cyanodimethylmethyl)-amino]-benzoic acid methyl ester (49b) (0.398 g, 1.95 mmol, 92%) as a white solid.

Workup

  1. temperaturewas refluxed for 15 hours
  2. filtrationAfter filtration
  3. customto remove the sodium sulfate
  4. washthe filtrate was washed with brine
  5. extractionextracted with ethyl acetate
  6. concentrationThe organic layer was concentrated
  7. customchromatographed (dichloromethane:acetone, 60:40)

Sources & evidence

ORD record
ord-f68d5d37ae96449f839e4a1d6302ae0f
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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