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-0235921bd5294f12b5a1302bd6533bfd

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557131B2