Potassium Phosphate, Tribasic → N-(3-morpholino-5-nitrophenyl)isobutyramide

HRID 1431784Notes

Reaction equation

HRID 1431784 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]([NH2:22])(=[O:21])[CH:18]([CH3:20])[CH3:19].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:22][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 68424IsobutyramideHCID 596310694-(3-Chloro-5-nitrophenyl)morpholine

Product 1

HCID 67507653N-(3-morpholino-5-nitrophenyl)isobutyramide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

Prepared according to Procedure W by stirring palladium (II) acetate (0.028 g, 0.124 mmol), tetramethyl tert-butyl XPhos (0.178 g, 0.371 mmol), 4-(3-chloro-5-nitrophenyl)morpholine (0.300 g, 1.236 mmol), isobutyramide (0.129 g, 1.484 mmol), potassium phosphate (0.367 g, 1.731 mmol), and tert-butanol (3 mL) at 110° C. for 4 h. Purification by column chromatography (silica; 0-30% EtOAc in hexanes) afforded N-(3-morpholino-5-nitrophenyl)isobutyramide as an orange amorphous solid. Mass Spectrum (ESI) m/e=293.9 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica; 0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-709ee07ee55544d5adeedbca4f1b6e56
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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