Ammonium Chloride → HCID 10062084, compound

HRID 1607665Notes

Reaction equation

HRID 1607665 reaction equation
[CH3:1][NH:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH:5]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][NH:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 11722781HCID 11722781, compound

Product 1

HCID 10062084HCID 10062084, compoundYield 100.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-methyl-3-(2,4-difluorophenoxy)-4-nitrobenzamide (0.85 g), iron powder (0.8 g) and ammonium chloride (80 mg) in ethanol (20 ml) and water (10 ml) was refluxed with stirring for an hour. The insoluble materials were filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated to give a powder of N-methyl-4-amino-3-(2,4-difluorophenoxy)benzamide (0.77 g).

Workup

  1. temperaturewas refluxed
  2. filtrationThe insoluble materials were filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ff09df76ef294574b2276cec484b4b39
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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