4-Methylmorpholine → N-[5-(Hydroxymethyl)-2-pyridinyl]acetamide

A solution of 219 mg (1.22 mmol) of 6-(acetylamino)nicotinic acid [preparable from 6-aminonicotinic acid according to A. Zafar et al., Tetrahedron 56, 8419-8428 (2000)] in 25.4 ml of dry THF is cooled to −10° C., and 123 mg (1.22 mmol) of 4-methylmorpholine and 132 mg (1.22 mmol) of ethyl chloroformate are added dropwise with stirring. The reaction solution is stirred at −10° C. for 30 min 2.44 ml (2.44 mmol) of a 1 M solution of lithium aluminium hydride and THF are then added dropwise. The reaction mixture is stirred for 8 h and slowly warmed to RT during this time. The reaction solution is then cooled to 0° C., 0.4 ml of water and 0.8 ml of 1 N aqueous sodium hydroxide solution are added carefully and, after warming to RT, the mixture is stirred at this temperature for 8 h. The mixture is filtered and the filtrate is concentrated on a rotary evaporator. The crude product that remains is used for the subsequent reaction without further purification.

1. additionare then added dropwise
2. stirringThe reaction mixture is stirred for 8 h
3. temperatureThe reaction solution is then cooled to 0° C.
4. temperatureafter warming to RT
5. stirringthe mixture is stirred at this temperature for 8 h
6. filtrationThe mixture is filtered
7. concentrationthe filtrate is concentrated on a rotary evaporator
8. customThe crude product that remains is used for the subsequent reaction without further purification

ORD record

ord-de4b465e039d45ea98ee8268d121368c

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653109B2