Ammonium Chloride → HCID 83853743, compound

HRID 2200199Notes

Reaction equation

HRID 2200199 reaction equation
[F:1][C:2]1([F:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[O:5][CH2:4][CH2:3]1.[Cl-].[NH4+]>CO.[Zn]>[F:15][C:2]1([F:1])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH2:12])[CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 90020202HCID 90020202, compound

Product 1

HCID 83853743HCID 83853743, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Dissolve 4,4-difluoro-6-nitro-chromane (2.5 g, 11.6 mmol) in methanol (100 mL), add zinc powder (2.5 g, 34.8 mmol), then add dropwise a 15.5% aqueous solution of ammonium chloride (40 mL, 139 mmol), stir at room temperature for 5 hrs. Filter off the solid, add water (50 mL) to the filtrate, extract with EtOAc (50 mL×2). Combine the organic layers, wash with brine (50 mL×2), dry over anhydrous Na2SO4. Concentrate under reduced pressure to get a crude residue. Purification by chromatography (silica gel, EtOAc:PE=1:3) affords the title compound (1.8 g, 83.7%). MS: (M+1): 186.2.

Workup

  1. filtrationFilter off the solid
  2. additionadd water (50 mL) to the filtrate
  3. extractionextract with EtOAc (50 mL×2)
  4. washCombine the organic layers, wash with brine (50 mL×2)
  5. dry with materialdry over anhydrous Na2SO4
  6. concentrationConcentrate under reduced pressure
  7. customto get a crude residue
  8. customPurification by chromatography (silica gel, EtOAc:PE=1:3)

Sources & evidence

ORD record
ord-75b4daeb3f39417c943d8f529461b7e3
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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