Ammonium Chloride → HCID 68521596, compound

HRID 1437434Notes

Reaction equation

HRID 1437434 reaction equation
[Br:1][C:2]1[C:3]([F:21])=[CH:4][C:5]([N+:18]([O-])=O)=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH3:10])[CH:7]=1.[Cl-].[NH4+].C([O-])(=O)C.[NH4+]>CO.C1COCC1.[Zn]>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH3:10])[C:5]([NH2:18])=[CH:4][C:3]=1[F:21]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 517165Ammonium AcetateHCID 68521412HCID 68521412, compound

Product 1

HCID 68521596HCID 68521596, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of (S)-5-bromo-4-fluoro-N-(1-(4-fluorophenyl)ethyl)-2-nitrobenzenamine (Method 46; 0.63 g, 1.76 mmol) and zinc dust (0.554 g, 8.47 mmol) in MeOH:THF (1:1, 24 ml) was slowly added the saturated ammonium chloride solution (4 ml). The reaction mixture was stirred at 25° C. for 2 hours followed by addition of saturated ammonium acetate solution (5 ml). The resulting mixture was stirred for another 30 minutes. Zn dust was removed by filtration and washed with EtOAc (20 ml). The organic layer was separated, washed with brine (10 ml), dried over Na2SO4, and concentrated under reduced pressure to give the crude product which was directly used for the next step without further purification. MS: Calcd.: 326. Found: [M+H]+ 327.

Workup

  1. stirringThe resulting mixture was stirred for another 30 minutes
  2. customZn dust was removed by filtration
  3. washwashed with EtOAc (20 ml)
  4. customThe organic layer was separated
  5. washwashed with brine (10 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d63911426e84c01a9a30fb4cfad3aab
Source dataset
uspto-grants-2009_11
Patent number
US07622482B2

Reaction notes

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