Hydrochloric Acid → 2-(Aminomethyl)-5-chloro-4-nitrobenzenamine

HRID 59378Notes

Reaction equation

HRID 59378 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([NH2:6])=O.Cl.[OH-].[Na+]>C1COCC1>[NH2:6][CH2:4][C:3]1[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]([Cl:11])=[CH:10][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10751185HCID 10751185, compound

Product 1

HCID 900190742-(Aminomethyl)-5-chloro-4-nitrobenzenamineYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-chloro-5-nitrobenzamide (3.0 g, 13.7 mmol) in dry THF (50 mL), borane dimethyl sulphide complex (1.56 g, 20.6 mmol) was added at RT and the reaction mass was refluxed for 24 h. The reaction mass was cooled to RT and dilute HCl was added till it became acidic. Further, the reaction mixture was stirred for 1 h and then the reaction mixture was basified with dilute NaOH and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 2.0 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 3.58 (s, 2H), 6.72 (br s, 3H), 8.04 (br s, 1H); MS (m/z): 200.28 (M−H).

Workup

  1. temperaturethe reaction mass was refluxed for 24 h
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9688e8207079452293aebd261d27162b
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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