Ammonium Chloride → HCID 67070111, compound

HRID 2390825Notes

Reaction equation

HRID 2390825 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[C:5]([O:12][CH3:13])=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.[NH4+].[Cl-]>CO.O.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([O:12][CH3:13])=[C:4]([CH:3]=1)[CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67069940HCID 67069940, compound

Product 1

HCID 67070111HCID 67070111, compoundYield 134.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

step 3 To a solution of 116 (0.19 g, 0.49 mmol) in MeOH-water (1:1, 20 mL) was added NH4Cl (0.26 g, 4.9 mmol) and iron powder (0.14 g, 2.5 mmol). The resulting mixture was heated at reflux and stirred for 1 h. After cooling to RT, the mixture was filtered through a pad of diatomaceous earth which was washed with MeOH. The filtrate was concentrated under reduced pressure and the resulting aqueous fraction was extracted with EtOAc. The extracts were washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.24 g (64%) of 4-(5-bromo-3-tert-butyl-2-methoxybenzyloxy)phenylamine (118) as a yellow oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux
  3. filtrationthe mixture was filtered through a pad of diatomaceous earth which
  4. washwas washed with MeOH
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. extractionthe resulting aqueous fraction was extracted with EtOAc
  7. washThe extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude residue was purified by SiO2 chromatography
  12. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-6315fbbee21f426780ae8731a5641e0f
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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