반응 #11449

반응 방정식

tert-butyl 4-aminobutylcarbamate

2,4-dichloro-5,6-dimethyl-3-nitropyridine

triethylamine

→

tert-butyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butylcarbamate

수율 48.0%

용매

N,N-dimethylformamide

N,N-dimethylformamide

반응 조건

후처리

1. 1
   농축concentrated under reduced pressure
2. 2
   기타The residue was partitioned between water and ethyl acetate
3. 3
   기타The layers were separated
4. 4
   추출the aqueous layer was extracted with ethyl acetate
5. 5
   세척washed with brine
6. 6
   농축concentrated under reduced pressure
7. 7
   기타to provide a brown oily residue
8. 8
   기타This material was purified by flash chromatography (400 mL silica gel
9. 9
   세척eluting initially with 10% ethyl acetate in hexane
10. 10
    온도increasing the gradient to 15%

실험 절차

A solution of tert-butyl 4-aminobutylcarbamate (8.52 g, 45.24 mmol) in N,N-dimethylformamide was added to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (10.00 g, 45.24 mmol) and triethylamine (12.6 mL, 90.5 mmol) in N,N-dimethylformamide (320 mL). The reaction mixture was stirred overnight and then concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organics were combined, washed with brine and then concentrated under reduced pressure to provide a brown oily residue. This material was purified by flash chromatography (400 mL silica gel, eluting initially with 10% ethyl acetate in hexane and then increasing the gradient to 15% and then to 25%) to provide 8.1 g of tert-butyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butylcarbamate as a yellow solid.

출처