Ammonium Chloride → HCID 86719577, compound

HRID 2208925Notes

Reaction equation

HRID 2208925 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([N+:17]([O-])=O)[C:9]([CH3:16])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:17][C:8]1[C:9]([CH3:16])=[C:10]([CH:15]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 70874088HCID 70874088, compound

Product 1

HCID 86719577HCID 86719577, compoundYield 106.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To stirred solution of methyl 5-(2-methoxyethoxy)-2-methyl-3-nitrobenzoate (1.35 g, 4.83 mmol) in ethanol (20 mL) were added ammonium chloride (1.35 g, 25.0 mmol) dissolved in water (20 mL) and iron powder (1.07 g, 19.3 mmol). The resulting reaction mixture was heated at 80° C. for 3 h. On completion, the reaction mixture was filtered and the residue washed well with hot ethanol. The filtrate was concentrated and the residue was basified by aqueous sodium bicarbonate. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with water, dried, concentrated under reduced pressure to give the crude title compound (1.23 g) which was used directly in the next step.

Workup

  1. customThe resulting reaction mixture
  2. filtrationOn completion, the reaction mixture was filtered
  3. washthe residue washed well with hot ethanol
  4. concentrationThe filtrate was concentrated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washThe combined organic layers were washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-503631351f904f268b101a7f5336e0b4
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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