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

HRID 1410211Notes

Reaction equation

HRID 1410211 reaction equation
B.C1COCC1.[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17].CO.Cl>C1COCC1>[ClH:7].[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 2723981Borane;tetrahydrofuran

Product 1

HCID 18796739(4-Chloro-3-nitrobenzyl)amine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BH3/THF (279 mL; 279 mmol) was added to a solution of 4-chloro-3-nitrobenzonitrile (30 g; 164 mmol) in THF (100 mL) over 30 min at 0° C. and the resulting mixture was stirred over night and allowed to reach rt. MeOH (150 mL) and conc. HCl (60 mL) was added and the resulting mixture was refluxed for 4 h and thereafter concentrated. The residue was treated with water (500 mL) and the resulting precipitate was filtered off. The filtrate was treated with NaCl (120 g) and heated and the resulting precipitate was filtered off to give the sub-title compound. Yield: 24.059 g (65%).

Workup

  1. customto reach rt
  2. temperaturethe resulting mixture was refluxed for 4 h
  3. concentrationconcentrated
  4. additionThe residue was treated with water (500 mL)
  5. filtrationthe resulting precipitate was filtered off
  6. additionThe filtrate was treated with NaCl (120 g)
  7. temperatureheated
  8. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-821890d95d7f486586c6841d87f8fa76
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

Loading…