Aniline → 2-chloro-N-(2-methoxy-4-nitrophenyl)acetamide

Temperature

0 °C

2-Methoxy-4-nitroaniline (8.40 g, 50 mmol) was dissolved in 200 mL dichloromethane and stirred at 0° C. while adding diisopropylethylamine (6.45 g, 50 mmol) then a solution of chloroacetyl chloride (5.65 g, 50 mmol) in 50 mL dichloromethane. The mixture was stirred for 17 h at 20-25° C., evaporated and 300 mL ethyl acetate added. The solution was washed with 2×100 mL 2M hydrochloric acid then brine, dried (sodium sulphate) and evaporated. The residue dissolved in 200 mL warm toluene, charcoaled then chromatographed on 300 mL flash silica in a 10 cm sinter funnel. Elution with toluene and evaporation afforded a bright yellow oil which solidified on standing. NMR showed an 11:4 mixture of product and starting aniline—product δ 9.17(s, 1H), 8.56(m,1H), 7.94(m, 1H), 7.79(m, 1H), 4.22(s, 2H), 4.03(s, 3H). Used without further purification.

1. stirringThe mixture was stirred for 17 h at 20-25° C.
2. customevaporated
3. addition300 mL ethyl acetate added
4. washThe solution was washed with 2×100 mL 2M hydrochloric acid
5. dry with materialbrine, dried (sodium sulphate)
6. customevaporated
7. dissolutionThe residue dissolved in 200 mL
8. temperaturewarm toluene
9. customcharcoaled then chromatographed on 300 mL flash silica in a 10 cm sinter funnel
10. washElution
11. customwith toluene and evaporation
12. customafforded a bright yellow oil which
13. additionan 11:4 mixture of product
14. customUsed without further purification

ORD record

ord-560be54474f94f8ea90170edca178ffb

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07442698B2