Ammonium Chloride → N-(3-Amino-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide

HRID 1258748Notes

Reaction equation

HRID 1258748 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[O:18][C:19]([F:22])([F:21])[F:20])[CH2:7][NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])([O-])=O.[NH4+].[Cl-]>[Fe].CCO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[O:18][C:19]([F:20])([F:21])[F:22])[CH2:7][NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67975181N-(3-Nitro-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide

Product 1

HCID 67975180N-(3-Amino-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(3-nitro-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide (3.4 g, 11 mmol), Fe (3.7 g, 66 mmol), saturated aqueous NH4Cl-solution (35 mL) and EtOH (170 mL) was refluxed for 30 min. The mixture was concentrated, treated with water and the pH was adjusted to ˜8. The mixture was extracted with EtOAc and the organic layer was dried over Na2SO4, filtered and concentrated. The residue was treated with PE and the sub-title compound was filtered off. Yield: 2.7 g (88%).

Workup

  1. temperaturewas refluxed for 30 min
  2. concentrationThe mixture was concentrated
  3. additiontreated with water
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionThe residue was treated with PE
  9. filtrationthe sub-title compound was filtered off

Sources & evidence

ORD record
ord-9f27d2f71dab47fcb810ceb7dbe3d51b
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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