Ammonium Chloride → HCID 126739807, compound

HRID 1481269Notes

Reaction equation

HRID 1481269 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C@@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:18][CH:19]=[CH2:20])[CH:12]=1.[Cl-].[NH4+]>CO.[Zn]>[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C@@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:18][CH:19]=[CH2:20])[CH:12]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 66745235HCID 66745235, compound

Product 1

HCID 126739807HCID 126739807, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a clear, orange solution of 1D (2.9 g, 7.54 mmol) in methanol (75 mL) was added sequentially zinc dust (4.93 g, 75 mmol) and ammonium chloride (4.04 g, 75 mmol). The resulting suspension was stirred vigorously for 4 h. The reaction was yellow filtrate. Concentration of the filtrate gave a yellow-black residue. The residue was partitioned between EtOAc and 0.25 M HCl (50 mL) and the layers were separated. The organic layer was extracted with 0.25 M HCl (1×50 mL). The combined aqueous layers were basified with 1.5M K2HPO4 and then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give 1E (2.63 g, 98%) as a brown foam. MS (ESI) m/z: 355.2 (M+H)+.

Workup

  1. customConcentration of the filtrate gave a yellow-black residue
  2. customThe residue was partitioned between EtOAc and 0.25 M HCl (50 mL)
  3. customthe layers were separated
  4. extractionThe organic layer was extracted with 0.25 M HCl (1×50 mL)
  5. extractionextracted with EtOAc (3×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f5ae2a4309844b7691cfeab5fd626d06
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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