Reaction #1973961

Reaction equation

Methyl 3-tert-butyl-2-methoxy-5-nitrobenzoate

ammonium chloride

water

→

title compound

Yield 100.0%

methyl 5-amino-3-tert-butyl-2-methoxybenzoate

Yield 100.0%

Solvents

methanol

Conditions

Workup

1. 1
   Filtrationfiltered through celite
2. 2
   Washthe celite washed with methanol
3. 3
   ConcentrationThe filtrate was then concentrated under vacuum
4. 4
   workup.DISSOLUTIONdissolved in ethyl acetate (600 mL)
5. 5
   WashThe resultant solution was then washed with water and brine
6. 6
   ExtractionThe organic extract
7. 7
   Otherwas then dried
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated under vacuum

Procedure

Methyl 3-tert-butyl-2-methoxy-5-nitrobenzoate (10.42 g, 39.0 mmol), iron powder (325 mesh, 10.89 g, 195 mmol), ammonium chloride (3.13 g, 58.5 mmol), water (30 mL), and methanol (150 mL) were added together. The resultant mixture was then refluxed for 1 h. The mixture was then cooled to room temperature, filtered through celite, and the celite washed with methanol. The filtrate was then concentrated under vacuum and dissolved in ethyl acetate (600 mL). The resultant solution was then washed with water and brine. The organic extract was then dried, filtered and concentrated under vacuum to yield the title compound as an oil (9.25 g, 100%).

Source