Acetic Acid → (E)-4-(Dimethylamino)-N-(2-fluoro-3-(2-nitrovinyl)phenyl)benzamide

HRID 2361352Notes

Reaction equation

HRID 2361352 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1[CH:20]=[CH:19][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=O)[C:11]=2[F:18])=[O:8])=[CH:5][CH:4]=1.[N+:22]([CH3:25])([O-:24])=[O:23].C([O-])(=O)C.[NH4+].C(O)(=O)C>>[CH3:1][N:2]([CH3:21])[C:3]1[CH:20]=[CH:19][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12](/[CH:16]=[CH:25]/[N+:22]([O-:24])=[O:23])[C:11]=2[F:18])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 866815234-(Dimethylamino)-N-(2-fluoro-3-formylphenyl)benzamide

Product 1

HCID 67994595(E)-4-(Dimethylamino)-N-(2-fluoro-3-(2-nitrovinyl)phenyl)benzamideYield 31%

Procedure

A mixture of 4-(dimethylamino)-N-(2-fluoro-3-formylphenyl)benzamide (1.83 g, the crude product from previous step), nitromethane (0.859 mL, 15.98 mmol), and ammonium acetate (1.232 g, 15.98 mmol) in acetic acid (25 mL, 52.4 mmol) was heated at 100° C. for 2 hr. Acetic acid was removed under vacuum. To the residue was added CH2Cl2 (60 mL) and water (60 mL) and the mixture was basified with solid Na2CO3 to pH 9. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organic phase was washed with saturated NaHCO3 solution (40 mL) and brine (40 mL), and dried over anhydrous MgSO4. The desired product (0.786 g, 31% over 2 steps) was isolated by ISCO (120 g silica gel, 0-5% ethyl acetate/CH2Cl2) as a red solid.

Workup

  1. customAcetic acid was removed under vacuum
  2. additionTo the residue was added CH2Cl2 (60 mL) and water (60 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×50 mL)
  5. washThe combined organic phase was washed with saturated NaHCO3 solution (40 mL) and brine (40 mL)
  6. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-48348339f7d74154a2b9329ebb2669f2
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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