Sodium Hydroxide → (2,4-Dichloro-3-nitrophenyl)methanamine

HRID 410066Notes

Reaction equation

HRID 410066 reaction equation
[N+:1]([C:4]1[C:5]([Cl:19])=[C:6]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:7][NH:8]C(=O)C(F)(F)F)([O-:3])=[O:2].[OH-].[Na+]>CO>[N+:1]([C:4]1[C:5]([Cl:19])=[C:6]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:7][NH2:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 56839981N-(3-Nitro-2,4-dichloro-benzyl)-2,2,2-trifluoroacetamide

Product 1

HCID 56839971(2,4-Dichloro-3-nitrophenyl)methanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(3-nitro-2,4-dichloro-benzyl)-2,2,2-trifluoroacetamide (0.66 g, impure, content ˜50%), 4M NaOH-solution (1.3 mL, 5.2 mmol) and MeOH (15 mL) is refluxed for 4 h. Then the mixture is concentrated, diluted with water, acidified with 4M HCl, filtered, 4M NaOH-solution is added and it is extracted with EtOAc. The organic phase is dried with Na2SO4, filtered and concentrated. Yield 0.17 g

Workup

  1. temperatureis refluxed for 4 h
  2. concentrationThen the mixture is concentrated
  3. additiondiluted with water
  4. filtrationfiltered
  5. addition4M NaOH-solution is added
  6. extractionit is extracted with EtOAc
  7. dry with materialThe organic phase is dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9cc292976eae4befa2ee1517a8bd3287
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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