Water → HCID 57419450, compound

HRID 2280593Notes

Reaction equation

HRID 2280593 reaction equation
[C:1]([C:5]1[C:6]([O:18][CH3:19])=[C:7]([CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].O>[Fe].CO>[NH2:15][C:13]1[CH:14]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([O:18][CH3:19])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 57419449HCID 57419449, compound

Product 1

HCID 57419450HCID 57419450, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

Methyl 3-tert-butyl-2-methoxy-5-nitrobenzoate (10.42 g, 39.0 mmol), iron powder (325 mesh, 10.89 g, 195 mmol), ammonium chloride (3.13 g, 58.5 mmol), water (30 mL), and methanol (150 mL) were added together. The resultant mixture was then refluxed for 1 h. The mixture was then cooled to room temperature, filtered through celite, and the celite washed with methanol. The filtrate was then concentrated under vacuum and dissolved in ethyl acetate (600 mL). The resultant solution was then washed with water and brine. The organic extract was then dried, filtered and concentrated under vacuum to yield the title compound as an oil (9.25 g, 100%).

Workup

  1. filtrationfiltered through celite
  2. washthe celite washed with methanol
  3. concentrationThe filtrate was then concentrated under vacuum
  4. dissolutiondissolved in ethyl acetate (600 mL)
  5. washThe resultant solution was then washed with water and brine
  6. extractionThe organic extract
  7. customwas then dried
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f153d7f6bfd9482fb31b27537cf29aae
Source dataset
uspto-grants-2015_09
Patent number
US09139536B2

Reaction notes

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