Methylamine hydrochloride → 2-Amino-6-morpholino-3-nitroisonicotinic acid
Reaction equation
CC([O-])(C)C.[K+].[O:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[C:15]([C:19]([N+:22]([O-:24])=[O:23])=[CH:20][N:21]=2)[C:16]([OH:18])=[O:17])[CH2:9][CH2:8]1.[NH2:25]C.Cl>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH2:25][C:20]1[C:19]([N+:22]([O-:24])=[O:23])=[C:15]([CH:14]=[C:13]([N:10]2[CH2:11][CH2:12][O:7][CH2:8][CH2:9]2)[N:21]=1)[C:16]([OH:18])=[O:17]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
To a solution of Cu(OAc)2 (1.01 g, 5.6 mmol) and t-BuOK (21.95 g, 196 mmol) in DMF (200 mL) was added a solution of 2-morpholino-5-nitroisonicotinic acid (5.66 g, 28 mmol) and NH2CH3.HCl (4.65 g, 56 mmol) in DMF (100 mL) at 60° C. dropwise. The mixture was then stirred at 60° C. for 16 h. LCMS showed the desired product. It was cooled to room temperature and filtered. The filter cake was dissolved with water (250 mL) and acidified with aq. HCl solution to pH=1. It was then extracted with DCM/MeOH (400/100 mL×8). The organic layer was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with MeOH/DCM=1/10 to afford the crude product as a black oil (4.5 g); LC/MS: MS (ES+) m/e 269 (MH+).
Sources & evidence
- ORD record
- ord-89652c27e1ad447d9d349943af3a6e7f
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906910B2
Reaction notes
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