Acetic acid ethanol → HCID 178519433, compound

HRID 2075257Notes

Reaction equation

HRID 2075257 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=O)[C:16]2[CH:21]=[CH:20][C:19]([CH:22](OC)[O:23]C)=[CH:18][C:17]=2[F:27])=[C:10]([N+:29]([O-])=O)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(O)=O.CCO>O.CCOC(C)=O.[Cl-].[Na+].O.[Fe]>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]2[NH:14][C:15]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][C:17]=3[F:27])=[N:29][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 18476134Acetic acid ethanol2×HCID 58415379HCID 58415379, compound

Product 1

HCID 178519433HCID 178519433, compound

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

To a yellow-orange solution of N-(4-benzyl-2-nitrophenyl)-4-(dimethoxymethyl)-2-fluorobenzamide (0.466 g, 1.1 mmol) in 5 mL 3:2 AcOH/EtOH was added iron powder—325 mesh (0.078 mL, 11 mmol). The reaction was fitted with a reflux condensor and was stirred rapidly at 120° C. bath. The reaction became a nearly solid mass after 10 min, and 3 mL 2:1 AcOH/EtOH was added to promote stirring. After 3 h, the mixture was bright yellow. The reaction was diluted with water, EtOAc, and brine, and the layers were separated. The aqueous layer was extracted 2× EtOAc, and the combined organics were washed 2×1N NaOH and 1× brine, dried over sodium sulfate, filtered, and concentrated to an orange oil. The material was purified by silica gel chromatography, ISCO, 40 g, 0-40% 90/10 DCM/MeOH in DCM to give title compound. MS (ESI) m/z: Calculated: 332.1; Observed: 333.1 (M++1).

Workup

  1. customThe reaction was fitted with a reflux condensor
  2. customafter 10 min
  3. stirringto promote stirring
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted 2× EtOAc
  6. washthe combined organics were washed 2×1N NaOH and 1× brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to an orange oil
  10. customThe material was purified by silica gel chromatography, ISCO, 40 g, 0-40% 90/10 DCM/MeOH in DCM

Sources & evidence

ORD record
ord-9b40e8f6bf47426da0227cdfbb864370
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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