Hydrochloric Acid → 2-Chloro-5-methylaniline

HRID 1898304Notes

Reaction equation

HRID 1898304 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-])=O.Cl.C([O-])(O)=O.[Na+]>CO.O.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH2:9]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 69764-Chloro-3-nitrotolueneHCID 516892Sodium Bicarbonate

Product 1

HCID 667702-Chloro-5-methylanilineYield 60.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-chloro-4-methyl-2-nitrobenzene (10.0 g, 0.058 mol) in methanol (50 mL), iron powder (3.0 g, 0.055 mol) and conc. HCl (10 mL) were added. The reaction mixture was stirred at RT for 2 h. The reaction mixture was diluted with water and basified with NaHCO3 solution and extracted with DCM. The organic layer was separated and dried over anhydrous sodium sulphate and concentrated to afford 5.0 g of the desired compound. 1HNMR (CDCl3): δ 2.23 (s, 3H), 3.94 (s, 2H), 6.50 (d, J=7.8 Hz, 1H), 6.57 (s, 1H), 7.10 (d, J=7.8 Hz, 1H); MS [M+H]+: 142.25.

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1c3e5873651c41189e6cebb98e0525ab
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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