Ammonium Chloride → N-(4-chlorophenyl)benzene-1,2-diamine

HRID 1485372Notes

Reaction equation

HRID 1485372 reaction equation
[NH4+].[Cl-].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)=[CH:6][CH:5]=1>[Fe].CCO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]([NH2:17])=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 89958N-(4-chlorophenyl)-2-nitroaniline

Product 1

HCID 522323N-(4-chlorophenyl)benzene-1,2-diamineYield 93.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of EtOH (100 ml) and NH4Cl saturated solution (15 ml), N-(4-chlorophenyl)-2-nitrobenzenamine (5.0 g, 20.1 mmol) was added, followed by iron powder (4.0 g). The reaction mixture was heated at 70° C. for 2 h. The solid was filtered and the filtrate was extracted by EA (100 mL×3), dried over Na2SO4. After the solvent was removed, the mixture was purified by Combi-flash (PE:EA=5:1) to give N1-(4-chlorophenyl)benzene-1,2-diamine (4.1 g, 93.2%) as a light yellow solid. LRMS (M+H+) m/z: calcd 218.06. found 218. 1H NMR (300 MHz, CD3OD): δ 6.52-6.59 (m, 3H), 6.70-6.74 (m, 1H), 6.81-6.87 (m, 1H), 6.90-6.99 (m, 3H).

Workup

  1. additionwas added
  2. filtrationThe solid was filtered
  3. extractionthe filtrate was extracted by EA (100 mL×3)
  4. dry with materialdried over Na2SO4
  5. customAfter the solvent was removed
  6. customthe mixture was purified by Combi-flash (PE:EA=5:1)

Sources & evidence

ORD record
ord-d6c952ab58ea434db107a05eae28d474
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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