Ammonium Chloride → HCID 22244730, compound

HRID 417316Notes

Reaction equation

HRID 417316 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([O:17][CH3:18])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CO.[Zn]>[C:1]([O:5][C:6](=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([O:17][CH3:18])[CH:9]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 22244737Tert-butyl (3-methoxy-4-nitrophenyl)acetate

Product 1

HCID 22244730HCID 22244730, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Step C A suspension of (3-methoxy-4-nitro-phenyl)-acetic acid tert-butyl ester (3 g, 11.2 mmol) in methanol (100 mL) was added an aqueous solution (50 mL) of NH4Cl (6 g, 112 mmol), followed by activated zinc (Aldrich, 7.3 g, 112 mmol). The reaction mixture was stirred at room temperature for 0.5 h. The mixture was filtered through a short pad of celite. The mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, and aqueous layer was extracted with ethyl acetate. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated to give (4-amino-3-methoxy-phenyl)-acetic acid tert-butyl ester as a brown oil (2.5 g, 94%).

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe mixture was concentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionaqueous layer was extracted with ethyl acetate
  6. extractionThe combined organic extract
  7. washwas washed with water, brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-add844846f8b405aa0cca66df091eecd
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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