Ammonium Chloride → HCID 117761100, compound

HRID 523229Notes

Reaction equation

HRID 523229 reaction equation
[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[C:11]=2[N+:18]([O-])=O)[CH:5]=[CH:6][CH:7]=1.[NH4+].[Cl-]>CO.[Zn]>[NH2:18][C:11]1[C:12]([F:17])=[CH:13][C:14]([F:16])=[CH:15][C:10]=1[C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[CH3:22])=[O:21]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 117760944HCID 117760944, compound

Product 1

HCID 117761100HCID 117761100, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(3-bromo-2-methylphenyl)-3,5-difluoro-2-nitrobenzamide (821 mg, 2.21 mmol), NH4Cl (1.18 g, 22.1 mmol) and zinc (1.45 g, 22.1 mmol) in MeOH (10 mL) was stirred at room temperature for 60 min. The mixture was filtered and the filtrate was concentrated. The residue was suspended in DCM and washed with saturated aqueous NaHCO3. The organic phase, with an insoluble precipitate, was separated from the aqueous phase and concentrated to give 2-amino-N-(3-bromo-2-methylphenyl) -3,5-difluorobenzamide (760 mg), used without further purification. Mass spectrum m/z 341, 343 (M+H)+, 363, 365 (M+Na)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. washwashed with saturated aqueous NaHCO3
  4. customThe organic phase, with an insoluble precipitate, was separated from the aqueous phase
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb76bf10e5f3487caf2b26da65424186
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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