Ammonium Chloride → HCID 84665992, compound

HRID 2208918Notes

Reaction equation

HRID 2208918 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N+:14]([O-])=O)[C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:14][C:5]1[C:6]([CH3:13])=[C:7]([CH:12]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 53399479Benzoic acid, 5-methoxy-2-methyl-3-nitro-, methyl ester

Product 1

HCID 84665992HCID 84665992, compoundYield 80.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-methoxy-2-methyl-3-nitrobenzoate (1.7 g, 7.6 mmol) in ethanol (20 mL) was added ammonium chloride (1.7 g, 32 mmol) dissolved in water (20 mL) and iron powder (3.38 g, 60.44 mmol). The mixture was heated at 80° C. for 3 h, filtered and the residue washed well with hot ethanol. The filtrate was concentrated and the residue was basified with 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 to give the crude title compound (1.2 g) which was used directly in the next step.

Workup

  1. filtrationfiltered
  2. washthe residue washed well with hot ethanol
  3. concentrationThe filtrate was concentrated
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4eeb3cc9326e4c23b233baf73eaf3899
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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