반응 #60242

반응 방정식

4-Amino-3-fluoro-5-nitro-2-o-tolylamino-benzoic acid methyl ester

formic acid

formic acid

→

7-Fluoro-6-o-tolylamino-1H-benzoimidazole-5-carboxylic acid methyl ester

용매

EtOH

반응 조건

후처리

1. 1
   온도the reaction mixture is cooled to room temperature
2. 2
   온도The reaction mixture is heated to 95° C.
3. 3
   workup.STIRRINGwith stirring
4. 4
   workup.WAITAfter 16 hours
5. 5
   온도the reaction mixture is cooled to room temperature
6. 6
   여과filtered through Celite
7. 7
   세척rinsing with EtOH
8. 8
   농축The filtrate is concentrated under reduced pressure until the desired product
9. 9
   기타precipitates
10. 10
    여과The desired product is collected by filtration
11. 11
    농축The filtrate is concentrated again until more desired product
12. 12
    기타precipitates
13. 13
    여과The product is collected by filtration
14. 14
    농축Repeated EtOH concentration, product filtration several times
15. 15
    기타Recovered 1.09 g (74%) pure desired product

실험 절차

4-Amino-3-fluoro-5-nitro-2-o-tolylamino-benzoic acid methyl ester 5a (1.57 g, 4.92 mmol), formic acid (25 mL, 26.5 mmol) and 20% Pd(OH)2/C (1.57 g, 2.95 mmol) in 25 mL EtOH are heating with stirring to 95° C. After 16 hours, the reaction mixture is cooled to room temperature and 0.5 g 20% Pd(OH)2/C and 10 mL formic acid added. The reaction mixture is heated to 95° C. with stirring. After 16 hours, the reaction mixture is cooled to room temperature and filtered through Celite rinsing with EtOH. The filtrate is concentrated under reduced pressure until the desired product precipitates. The desired product is collected by filtration. The filtrate is concentrated again until more desired product precipitates. The product is collected by filtration. Repeated EtOH concentration, product filtration several times. Recovered 1.09 g (74%) pure desired product: MS APCI (+) m/z 300 (M+1) detected; MS APCI (−) m/z 298 (M−1) detected.

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