Ammonium Chloride → Methyl 3-amino-5-chloro-2-methylbenzoate

HRID 2208754Notes

Reaction equation

HRID 2208754 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:13]([O-])=O)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:13][C:4]1[C:5]([CH3:12])=[C:6]([CH:11]=[C:2]([Cl:1])[CH:3]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 53399191Methyl 5-chloro-2-methyl-3-nitrobenzoate

Product 1

HCID 68295455Methyl 3-amino-5-chloro-2-methylbenzoateYield 87.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To stirred solution of methyl 5-chloro-2-methyl-3-nitrobenzoate (16 g, 69 mmol) in ethanol (160 mL), ammonium chloride (16 g, 53.4 mmol) dissolved in water (160 mL) and iron powder (31.2 g, 55.85 mmol) were added under stirring. The resulting reaction mixture was heated at 80° C. for 1 h. On completion, water was added to and the reaction mixture filtered through celite. The filtrate was extracted with ethyl acetate and the combined organic layers washed with water, dried and concentrated under reduced pressure giving desired compound (12.10 g, 86%) without further purification.

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered through celite
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthe combined organic layers washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-65b556871f194e8599c1d8cf63375b10
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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