Acetic Acid → HCID 66914350, compound

HRID 2104592Notes

Reaction equation

HRID 2104592 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[C:26]([F:29])([F:28])[F:27])=[O:9])=[CH:4][CH:3]=1.[OH2:30].CC(O)=[O:33]>>[N+:1]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[C:26]([F:29])([F:27])[F:28])=[O:9])=[CH:4][CH:3]=1)([O-:33])=[O:30]

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 962WaterHCID 66913663HCID 66913663, compound

Product 1

HCID 66914350HCID 66914350, compound

Procedure

(4-Aminophenyl)[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone (0.050 g, 0.127 mmol) in AcOH (2 mL) is added slowly to a stirred solution of NaBO3 4H2O (0.098 g, 0.637 mmol) in AcOH (3 mL) at 55° C. over 40 min. After 1 h, the reaction is cooled, poured into water and extracted with methylene chloride. The extracts are washed with saturated aq sodium bicarbonate, dried over MgSO4 and concentrated. The residue is purified by chromatography eluting with 10:90 ethyl acetate:hexane to afford the title compound (0.0157 g). MS (ESI) m/z 423; HRMS: calcd for C23H13F3N2O3+H, 423.09565; found (ESI, [M+H]+), 423.0943.

Workup

  1. temperaturethe reaction is cooled
  2. extractionextracted with methylene chloride
  3. washThe extracts are washed with saturated aq sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography
  7. washeluting with 10:90 ethyl acetate

Sources & evidence

ORD record
ord-2680b9e1b9764d1b8df1683ef3f8ee1a
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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