Реакция #41802

Уравнение реакции

water

NaOH

water

t-butyl ester

2-Fluoro-3-(4-methyl-piperazin-1-yl)-6-nitro-phenylamine

LAH

→

2

3-Fluoro-4-(4-methyl-piperazin-1-yl)-benzene-1,2-diamine

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   ДругоеA flame dried 500 mL three-necked round bottom flask
2. 2
   Другоеpurged with N2
3. 3
   workup.ADDITIONwas slowly added
4. 4
   Другоеunder 5° C
5. 5
   workup.WAITat rt for 30 min
6. 6
   ФильтрацияThe resulting suspension was filtered through Celite
7. 7
   Промывкаwashed with ethyl acetate and methanol
8. 8
   ДругоеThe crude product was absorbed onto silica gel
9. 9
   Другоеpurified by flash chromatography (97:3 CH2Cl2/MeOH)

Методика

A flame dried 500 mL three-necked round bottom flask purged with N2 was charged with LAH (2.32 g, 58.0 mmol) and dry THF (60 mL). The resulting suspension was cooled to 0° C. and a suspension of t-butyl ester 1 (10.0 g, 29.0 mmol) in dry THF (60 mL) was slowly added while keeping the internal reaction temperature under 5° C. The reaction was stirred at 0° C. for 30 min then at rt for 30 min. After the reaction was judged complete, the mixture was treated with successive dropwise addition of water (2.3 mL), 10% NaOH (2.3 mL), and water (7.2 mL). The resulting suspension was filtered through Celite, washed with ethyl acetate and methanol, and the collected organics concentrated. The crude product was absorbed onto silica gel and purified by flash chromatography (97:3 CH2Cl2/MeOH) to give 2 as an orange solid: 1H NMR (300 MHz, CDCl3) δ 8.40 (d, J=5.5 Hz, 1H), 8.05 (br s, 1H), 7.96 (d, J=2.75 Hz, 1H), 7.29 (d, J=2.75 Hz, 1H), 6.92 (d, J=9.35 Hz, 1H), 6.75 (m, 2H), 4.68 (s, 2H), 3.07 (d, J=5.23 Hz, 3H).

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