Reaction #80291

Reaction equation

allyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methyl-3-nitroindol-4-carboxylate

hydrochloric acid

tin

→

desired product

Yield 79.3%

Allyl 3-Amino-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate

Yield 79.3%

Solvents

methanol

Conditions

Workup

1. 1
   FiltrationThe solid was filtered off
2. 2
   Concentrationresidue was concentrated under reduced pressure
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe organic layer was washed with water
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   OtherThe residue obtained by concentration under reduced pressure
7. 7
   Otherwas crystallized from isopropyl ether

Procedure

3.4 g of allyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methyl-3-nitroindol-4-carboxylate was dissolved in 50 ml of methanol, and 5 ml of concentrated hydrochloric acid was added thereto. Then, 4.9 g of tin powder was gradually added at room temperature. Them, the mixture was stirred at room temperature for 12 hours. The solid was filtered off, and then residue was concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2.5 g (yield: 79%) of the desired product. mp: 132°-135° C.

Source