反応 #11449

反応方程式

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

収率 48.0%

溶媒

N,N-dimethylformamide

N,N-dimethylformamide

反応条件

後処理

1. 1
   濃縮concentrated under reduced pressure
2. 2
   その他The residue was partitioned between water and ethyl acetate
3. 3
   その他The layers were separated
4. 4
   抽出the aqueous layer was extracted with ethyl acetate
5. 5
   洗浄washed with brine
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他to provide a brown oily residue
8. 8
   その他This material was purified by flash chromatography (400 mL silica gel
9. 9
   洗浄eluting initially with 10% ethyl acetate in hexane
10. 10
    温度increasing the gradient to 15%

実験手順

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.

出典