Dimethylformamide → 3-Hydroxy-2-methylbenzamide

Oxalyl chloride (4.19 ml, 48 mmol) was added to an ice-cold solution of 3-hydroxy-2-methylbenzoic acid (3.62 g, 24 mmol) in dichloromethane (30 mL). N,N-dimethylformamide (2 mL) was then added and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was concentrated in vacuo three times from toluene. The residue was then suspended in tetrahydrofuran (10 mL), added to ice-cold 0.88 ammonia solution (10 mL) and stirred for 2.5 hours, allowing the temperature to rise to ambient. The reaction mixture was then extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo and the residue was concentrated in vacuo from acetone and triturated with diethyl ether to afford the title compound as a solid in 45% yield. LRMS APCI m/z 152 [M+H]+

1. concentrationThe reaction mixture was concentrated in vacuo
2. concentrationthe residue was concentrated in vacuo three times from toluene
3. additionadded to ice-cold 0.88 ammonia solution (10 mL)
4. stirringstirred for 2.5 hours
5. extractionThe reaction mixture was then extracted with ethyl acetate
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. concentrationthe residue was concentrated in vacuo from acetone
9. customtriturated with diethyl ether

ORD record

ord-16c1b11d3e9749b294f3286c851f3794

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207198B2