Acetic Acid → 6-Chloro-N1-methylbenzene-1,2-diamine

HRID 334722Notes

Reaction equation

HRID 334722 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[NH:11][CH3:12].C(O)(=O)C>CCO.O.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:11][CH3:12]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 126932352-Chloro-N-methyl-6-nitroaniline

Product 1

HCID 126932366-Chloro-N1-methylbenzene-1,2-diamineYield 73.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Chloro-N-methyl-6-nitrobenzenamine (1.5 g, 8.0 mmol) was dissolved in a mixture of EtOH (15 mL) and H2O (15 ml). Iron powder (2.2 g, 40 mmol) was added followed by Acetic acid (0.55 mL, 9.6 mmol). The reaction was monitored by TLC, after 30 min, the reaction was completed. The reaction mixture was filtered over celite pad and the filtrate was neutralized by saturated NaHCO3 (10 mL). The product was extracted by EtOAc (2*10 mL), the organic layer was washed with brine (10 mL), dried over MgSO4 and concentrated to dryness to afford 920 mg of 6-chloro-N1-methylbenzene-1,2-diamine (Yield: 73%) as dark brown oil.

Workup

  1. filtrationThe reaction mixture was filtered over celite pad
  2. extractionThe product was extracted by EtOAc (2*10 mL)
  3. washthe organic layer was washed with brine (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5ea98f3e15d74182b6567a839a12b680
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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