Morpholine → (2-Amino-4-nitrophenyl)(morpholin-4-yl)methanone
Reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:7][C:8]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[NH2:7][C:8]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:9]=1[C:10]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Morpholine (2.152 mL, 24.71 mmol) was added to a stirred suspension of 2-amino-4-nitrobenzoic acid (1.5 g, 8.24 mmol) and HATU (3.44 g, 9.05 mmol) in acetonitrile (15 mL) at room temperature. After 1 h at room temperature, the mixture was quenched with saturated NH4Cl (50 mL) and extracted with EtOAc (100 mL). The EtOAc layer was washed with saturated NH4Cl (10 mL) and brine (10 mL), dried (MgSO4), and concentrated. The resulting syrup was triturated with hot CH2Cl2 and a yellow solid precipitated out. The solid was washed with CH2Cl2 and collected by filtration (1.7195 g, 83% yield). LCMS: (M+H)+=252.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.54 (1H, d, J=2.26 Hz), 7.35 (1H, dd, J=8.28, 2.26 Hz), 7.24 (1 H, d, J=8.53 Hz), 5.86 (2H, s), 3.60 (8H, br. s.).
Workup
- customthe mixture was quenched with saturated NH4Cl (50 mL)
- extractionextracted with EtOAc (100 mL)
- washThe EtOAc layer was washed with saturated NH4Cl (10 mL) and brine (10 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe resulting syrup was triturated with hot CH2Cl2
- customa yellow solid precipitated out
- washThe solid was washed with CH2Cl2
- filtrationcollected by filtration (1.7195 g, 83% yield)
Sources & evidence
- ORD record
- ord-3c4c385987894f89b891b3335e9efb09
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586751B2
Reaction notes
Loading…