Hydrochloric Acid → (4-Chloro-3-nitrobenzyl)amine hydrochloride

HRID 508779

Reaction equation

HRID 508779 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7]C(=O)C(F)(F)F)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].Cl>CO>[ClH:1].[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19879857N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamide

Product 1

HCID 18796739(4-Chloro-3-nitrobenzyl)amine hydrochlorideYield 221.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamide (0.800 g) in methanol (20 mL) was added conc. HCl (2.0 ml). The reaction mass was refluxed for 18 h. Excess solvent was removed under vacuum to afford 0.700 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 7.18 (s, 1H), 7.35 (s, 1H), 7.52 (s, 1H), 7.86 (s, 2H), 8.28 (s, 1H), 8.72 (br s, 2H).

Workup

  1. temperatureThe reaction mass was refluxed for 18 h
  2. customExcess solvent was removed under vacuum

Sources & evidence

ORD record
ord-34c81e3d4f8c47948ae2c6a9421f22d6
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Linked notes

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