Anthranilic Acid → Acetanthranil

HRID 2041002Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11](OC(=O)C)(=O)[CH3:12]>>[CH3:11][C:12]1[O:5][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[N:1]=1

Participants

Reactant 2

HCID 227Anthranilic Acid

HCID 7918Acetic Anhydride

Product 1

HCID 68236Acetanthranil

Procedure

A solution of 2-aminobenzoic acid (300 mg, 1.46 mmol) in acetic anhydride (2 mL) was heated to 130° C. for 16 hours. The mixture was concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 20% ethyl acetate in hexanes to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 2.44-2.52 (m, 3H), 7.44-7.60 (m, 2 H), 7.76-7.87 (m, 1H), 8.20 (dd, J=7.97, 1.53 Hz, 1H); MS (DCI/NH3) m/z 162 (M+H)+.

Workup

concentrationThe mixture was concentrated under reduced pressure
customThe residue was chromatographed on silica gel eluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-21e7f7665ca346d488d118d67751f5d9
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580968B2

Reaction notes

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