Ethanol → Methyl 3-amino-5-chloro-2-methylbenzoate

Temperature

90 °C

To a stirred solution of methyl 5-chloro-2-methyl-3-nitrobenzoate (1 equiv.) in ethanol (2 mL per 1 mmol), was added NH4Cl solution (5.1 equiv., dissolved in water. Volume of water equivalent to volume of ethanol) followed by Fe powder (8 equiv.). The resulting reaction mixture was stirred at 90° C. for 1 h. On completion, reaction mixture was filtered and the filtrate concentrated until dryness. The resulting solid which was dissolved in saturated sodium bicarbonate solution and the aqueous layer extracted with ethyl acetate. Combined organic layers were dried over sodium sulfate and concentrated to afford solid methyl 3-amino-5-chloro-2-methylbenzoate in quantitative yield.

1. customThe resulting reaction mixture
2. customOn completion, reaction mixture
3. filtrationwas filtered
4. concentrationthe filtrate concentrated until dryness
5. dissolutionThe resulting solid which was dissolved in saturated sodium bicarbonate solution
6. extractionthe aqueous layer extracted with ethyl acetate
7. dry with materialCombined organic layers were dried over sodium sulfate
8. concentrationconcentrated

ORD record

ord-83f0f1e419d14dfc83de9793491a4393

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206157B2