Acetamide → N-(3-morpholino-5-nitrophenyl)acetamide

HRID 1431754Notes

Reaction equation

HRID 1431754 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:17]([NH2:20])(=[O:19])[CH3:18].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(C)(C)C>[O:14]1[CH2:15][CH2:16][N:11]([C:4]2[CH:3]=[C:2]([NH:20][C:17](=[O:19])[CH3:18])[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 178AcetamideHCID 62657Potassium Phosphate, TribasicHCID 596310694-(3-Chloro-5-nitrophenyl)morpholine

Product 1

HCID 67507703N-(3-morpholino-5-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

Prepared according to Procedure V using palladium (II) acetate (0.013 g, 0.057 mmol), tetramethyl t-butyl XPhos (0.082 g, 0.170 mmol), 4-(3-chloro-5-nitrophenyl)morpholine (0.275 g, 1.133 mmol), acetamide (0.080 g, 1.360 mmol), tripotassium phosphate (0.337 g, 1.587 mmol), and tert-butanol (2.5 mL) to afford N-(3-morpholino-5-nitrophenyl)acetamide. No purification was performed. Mass Spectrum (ESI) m/e=266.1 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-851a56b2aa8f4c85a795ee5f43d6f94f
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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