3-bromo-N-cyclopropyl-5-nitropyridin-4-amine → 5-Bromo-N~4~-cyclopropylpyridine-3,4-diamine
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:12]([O-])=O)[C:7]=1[NH:8][CH:9]1[CH2:11][CH2:10]1>C(O)(=O)C.[Fe]>[Br:1][C:2]1[C:7]([NH:8][CH:9]2[CH2:11][CH2:10]2)=[C:6]([NH2:12])[CH:5]=[N:4][CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of the product obtained from Step 3 (2.95 g, 11.4 mmol) in glacial acetic acid (50 ml) was added iron dust (3.35 g, 60 mmol). The resulting mixture was stirred at 80° C. for 90 minutes, after which it was filtered through Celite and the liquor concentrated under vacuum. The crude product was re-dissolved in ethyl acetate, basified with sodium bicarbonate and refiltered. Th organic phase was washed with water three times, followed by twice with brine before concentrating under vacuum to give the product. Passed through a silica plug affording product as an oil, 1.65 g (63%); MS (ES+) m/e 228/230 [M+H]+.