反応 #68602

反応方程式

quinoline-6-carboxylic acid

oxalyl chloride

Hunig's Base

N-methoxymethanamine hydrochloride

→

N-methoxy-N-methylquinoline-6-carboxamide

収率 95.2%

溶媒

DCM

DCM

DCM

反応条件

後処理

1. 1
   濃縮concentrated
2. 2
   温度cooled to 0° C.
3. 3
   洗浄washed with water (250 mL), sat. NaHCO3 (250 mL), and brine (250 mL)
4. 4
   乾燥The organic layer was dried with MgSO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他to give a brown oil, which
8. 8
   その他was purified by MPLC
9. 9
   洗浄eluting with 2-6% MeOH/DCM

実験手順

A 250 mL RB flask was charged with quinoline-6-carboxylic acid (5.00 g, 28.9 mmol), DCM (100 ml, 1554 mmol), oxalyl chloride (3.79 ml, 43.3 mmol), and a few drops of DMF and stirred at RT for 2 hours, then concentrated. The residue was taken up in DCM (100 ml, 1554 mmol), cooled to 0° C., then Hunig's Base (17.7 ml, 101 mmol) and N-methoxymethanamine hydrochloride (2.96 g, 30.3 mmol) were added slowly. The mixture was stirred at room temperature for 16 hours (91463-3-1). The mixture was diluted with DCM (200 mL), then washed with water (250 mL), sat. NaHCO3 (250 mL), and brine (250 mL). The organic layer was dried with MgSO4, filtered, and concentrated to give a brown oil, which was purified by MPLC eluting with 2-6% MeOH/DCM to give N-methoxy-N-methylquinoline-6-carboxamide (5.943 g, 95.2% yield) as a brown oil.

出典