Ammonium Chloride → HCID 66387431, compound

HRID 2237512Notes

Reaction equation

HRID 2237512 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[NH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Zn]>[NH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][NH:4][C:3]1[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=1[F:1]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 28581760HCID 28581760, compound

Product 1

HCID 66387431HCID 66387431, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-fluoro-N-(2-nitrobenzyl)aniline (9.8 g, 40 mmol) in ethanol (200 mL) was treated with a solution of ammonium chloride (11 g, 66 mmol) in H2O (200 mL) and zinc dust (40 g, 66 mmol), and the reaction mixture was stirred at 50° C. for 2 h. The reaction mixture was filtered, diluted with ethyl ether (1 L), washed with H2O (1 L) and evaporated to provide N-(2-aminobenzyl)-2-fluoroaniline (8 g) as a pink solid:

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with ethyl ether (1 L)
  3. washwashed with H2O (1 L)
  4. customevaporated

Sources & evidence

ORD record
ord-04144a0ed3c74e95b00faf817a0ebd96
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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