Ammonia → 2-Methyl-2-(4-nitrophenoxy)propanamide

HRID 1770829Notes

Reaction equation

HRID 1770829 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][C:9]([CH3:14])([CH3:13])[C:10](O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC(OCC(C)C)=O.C([N:27](CC)CC)C.N>ClCCl.CO>[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][C:9]([CH3:14])([CH3:13])[C:10]([NH2:27])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 1769302-Methyl-2-(4-nitrophenoxy)propanoic acid

Product 1

HCID 123215222-Methyl-2-(4-nitrophenoxy)propanamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-nitrophenoxy)isobutyric acid (50) (5 g), isobutyl chloroformate (4.36 mL) and triethylamine (8 mL) in dichloromethane (20 mL) was stirred at room temperature for 1 hour. Then 2.0 M ammonia in methanol (20 mL) was added to the solution. The resulting solution was stirred at room temperature for 2 hours and then solvent was removed under reduced pressure. The mixture was purified by recrystallization from EtOAc and hexanes to give 2-(4-nitrophenoxy)-2-methylpropanamide (51).

Workup

  1. stirringThe resulting solution was stirred at room temperature for 2 hours
  2. customsolvent was removed under reduced pressure
  3. customThe mixture was purified by recrystallization from EtOAc and hexanes

Sources & evidence

ORD record
ord-95c7331352154b2bb40e3666e501c6b3
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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