Ammonium Chloride → HCID 86660317, compound

HRID 2365920Notes

Reaction equation

HRID 2365920 reaction equation
[Cl-].[NH4+].[CH2:3]([O:10][C:11]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]([N+:25]([O-])=O)=[CH:13][C:12]=1[F:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.[Zn]>[CH2:3]([O:10][C:11]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:14]([NH2:25])=[CH:13][C:12]=1[F:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 70921751HCID 70921751, compound

Product 1

HCID 86660317HCID 86660317, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

508 mg (9.5 mmol, 2 eq) of ammonium chloride, followed by 2.23 g (34.2 mmol, 7.2 eq) of zinc powder, are added to a solution of 1.68 g (4.75 mmol, 1 eq) of 1,5-bis(benzyloxy)-2-fluoro-4-nitrobenzene in 50 ml of water. The reaction medium is refluxed for 4 hours. The cooled reaction medium is extracted with ethyl acetate. The organic phases are combined, washed with a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and evaporated. The residue is chromatographed on silica gel, elution being carried out with 85/15 heptane/ethyl acetate.

Workup

  1. temperatureThe reaction medium is refluxed for 4 hours
  2. customThe cooled reaction medium
  3. extractionis extracted with ethyl acetate
  4. washwashed with a saturated solution of sodium chloride
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-8febeab18fb94554a884bc733a75bdb1
Source dataset
uspto-grants-2014_04
Patent number
US08697726B2

Reaction notes

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