Sodium Bicarbonate → HCID 89691166, compound

HRID 2202868Notes

Reaction equation

HRID 2202868 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([N:8]([CH3:14])[C:9](=O)[CH2:10][O:11][CH3:12])[CH:7]=1.[Cl-].[Cl-].[Ca+2].C([O-])(O)=O.[Na+]>CC(O)=O.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:15]=[C:9]([CH2:10][O:11][CH3:12])[N:8]([CH3:14])[C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5284359Calcium ChlorideHCID 89690341HCID 89690341, compound

Product 1

HCID 89691166HCID 89691166, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of N-(5-bromo-2-nitrophenyl)-2-methoxy-N-methylacetamide (477 mg) in AcOH (8 ml) was added zinc (400 mg) at 0° C. The mixture was stirred at 80° C. under a dry atmosphere (CaCl2 tube) for 3 h and then at room temperature overnight. The mixture was neutralized with saturated NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (306 mg) as a pale yellow oil.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-cd91a074851c47f0bf1a5a98d2fa88ea
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…