4-Aminobenzoic Acid → HCID 67132172, compound

HRID 1927365Notes

Reaction equation

HRID 1927365 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-3813e153e1894b128c88dda70334dd78
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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