Ammonium Chloride → HCID 86650697, compound

HRID 1873686Notes

Reaction equation

HRID 1873686 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([N+:28]([O-])=O)[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:22][CH3:23])=[C:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.[Cl-].[NH4+]>O.C(O)C.[Fe]>[NH2:28][C:26]1[CH:25]=[CH:24][C:3]([O:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:22][CH3:23])=[C:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:13]=3)[N:8]=[CH:7][CH:6]=2)=[C:2]([F:1])[CH:27]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86650695HCID 86650695, compound

Product 1

HCID 86650697HCID 86650697, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

Compound 1b (400 mg) was dissolved in a water-ethanol (1:1) mixture (10 mL), and iron powder (1.0 g) and ammonium chloride (1.0 g) were added thereto, followed by stirring at 80° C. for 2 hours. The reaction mixture was filtered through Celite to thereby remove iron powder, and water (100 mL) was added to the filtrate, followed by extraction with ethyl acetate (50 mL). The organic phase was washed with saturated brine (100 mL) and dried over sodium sulfate, followed by concentration under reduced pressure, to thereby yield compound 1c (335 mg, yield: 93%).

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was filtered through Celite to thereby remove iron powder, and water (100 mL)
  3. additionwas added to the filtrate
  4. extractionfollowed by extraction with ethyl acetate (50 mL)
  5. washThe organic phase was washed with saturated brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-0d21da34e8b747d3a19befdc562a65fa
Source dataset
uspto-grants-2012_11
Patent number
US08304427B2

Reaction notes

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