Ammonium Chloride → HCID 86719575, compound

HRID 2208921Notes

Reaction equation

HRID 2208921 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([N+:16]([O-])=O)[C:8]([CH3:15])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:16][C:7]1[C:8]([CH3:15])=[C:9]([CH:14]=[C:5]([O:4][CH2:3][CH2:2][OH:1])[CH:6]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 70873815HCID 70873815, compound

Product 1

HCID 86719575HCID 86719575, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-(2-hydroxyethoxy)-2-methyl-3-nitrobenzoate (1.5 g, 5.88 mmol) in ethanol (20 mL), were added ammonium chloride (1.5 g, 28 mmol) dissolved in water (20 mL) and iron powder (1.3 g, 23 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, and concentrated under reduced pressure giving the crude title compound (1.3 g) which was used directly.

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-e7a0197a88de4f5f8e8463d871e5f519
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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