4-Aminobenzoic Acid → HCID 67132172, compound

HRID 245017Notes

Reaction equation

HRID 245017 reaction equation
[C-:1]#[N:2].[Na+].[NH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.[C:14]1(=O)[CH2:17][CH2:16][CH2:15]1>C(O)(=O)C>[C:1]([C:14]1([NH:4][C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)[CH2:17][CH2:16][CH2:15]1)#[N:2]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 8929Sodium CyanideHCID 14496Cyclobutanone

Product 1

HCID 67132172HCID 67132172, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanide (0.245 g, 5 mmol) was added to a mixture of 4-aminobenzoic acid (0.274 g, 2 mmol) and cyclobutanone (0.21 g, 3 mmol) in 90% acetic acid (4.5 ml). The reaction mixture was stirred at room temperature for 15 hours. The mixture was washed with aqueous HCl (pH 2) and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to dryness under vacuum to yield 4-(1-cyanocyclobutylamino)benzoic acid (51a) (0.426 g, 1.97 mmol, 99%) as a white solid.

Workup

  1. washThe mixture was washed with aqueous HCl (pH 2)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-823cb04dd01043e3a58b15491c78df16
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

Loading…