Dimethylformamide → 5-Methoxy-2-nitrobenzamide

To a suspension of 5-methoxy-2-nitrobenzoic acid (7.5 g, 38.0 mmol) in anhydrous benzene (50 mL), was added thionyl chloride (3.8 mL, 52.05 mmol) followed by the addition of anhydrous DMF (0.4 mL). The resulting reaction mixture was refluxed for 5 h, upon which the volatiles were removed in vacuo. The residue was dissolved in anhydrous THF (60 mL) and added to an ice-cold saturated solution of ammonia in THF (60 mL). The resulting heterogeneous reaction mixture was allowed to warm room temperature and stirring was continued at RT for 48 h. The s volatiles were removed in vacuo and the residue was used without further purification for next step. HPLC retention time 3.29 mins.

1. customThe resulting reaction mixture
2. temperaturewas refluxed for 5 h, upon which the volatiles
3. customwere removed in vacuo
4. dissolutionThe residue was dissolved in anhydrous THF (60 mL)
5. additionadded to an ice-cold saturated solution of ammonia in THF (60 mL)
6. customThe s volatiles were removed in vacuo
7. customthe residue was used without further purification for next step

ORD record

ord-f5ad0370f67c4812b77b853b92e3092a

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440961B2