Ammonium Chloride → HCID 18763413, compound

HRID 431378Notes

Reaction equation

HRID 431378 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)([O-])=O.[In].[Cl-].[NH4+]>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH:7]=[C:8]([NH2:10])[CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 18763432HCID 18763432, compound

Product 1

HCID 18763413HCID 18763413, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3,5-dinitrophenyl) (4-bromophenyl)amine (0.34 g, 1.0 mmol) in ethanol (10 mL) was added indium (2.0 g, 17 mmol) followed by saturated ammonium chloride solution (3 mL) and the mixture stirred 12 h. At this time, TLC showed the reaction complete. The reaction mixture was then filtered through celite, concentrated and the residue dissolved in 50 mL CH2Cl2. The organic solution was washed with 50 mL water followed by 50 mL brine, dried over magnesium sulfate, filtered and concentrated to give 0.26 g (93%) of a brown oil, Rf 0.1 (1:1 hexane:ethyl acetate), which was carried directly to the next step.

Workup

  1. filtrationThe reaction mixture was then filtered through celite,
  2. concentrationconcentrated
  3. dissolutionthe residue dissolved in 50 mL CH2Cl2
  4. washThe organic solution was washed with 50 mL water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-037189ab6d104c389d654dbf9e844fd6
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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