HCID 18626075, compound → HCID 18626123, compound

HRID 1859651Notes

Reaction equation

HRID 1859651 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[N+:17]([O-])=O>C(O)(=O)C.[Zn]>[NH2:17][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:2]=1[F:1])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7]

Participants

4

Reactant 1

HCID 18626075HCID 18626075, compound

Product 1

HCID 18626123HCID 18626123, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (14 g) was added to a solution of 4-fluoro-3-nitro-N-phenyl-benzamide (1.99 g, 7.6 mmol) in acetic acid (80 mL) at 0° C. The mixture was stirred and allowed to warm to room temperature. After 4 hours, the mixture was filtered and the residue washed with ethyl acetate. The filtrate and washings were combined and taken to dryness by rotovap and the residue partitioned between ethyl acetate (200 mL) and saturated aqueous NaHCO3. The organic layer was washed with saturated brine, dried over MgSO4, filtered, and stripped of solvent. The residue was triturated in ethyl acetate/hexane and the suspended solid filtered off to afford the product (1.55 g); m.p. 167-170° C.

Workup

  1. filtrationthe mixture was filtered
  2. washthe residue washed with ethyl acetate
  3. customthe residue partitioned between ethyl acetate (200 mL) and saturated aqueous NaHCO3
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe residue was triturated in ethyl acetate/hexane
  8. filtrationthe suspended solid filtered off

Sources & evidence

ORD record
ord-d6b0b310a62d49eb9b4141557ecedee7
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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