Ammonium Hydroxide → HCID 15540504, compound

HRID 1595200Notes

Reaction equation

HRID 1595200 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](C2C=CN=CC=2)[C:9]([C:11]2[CH:16]=[CH:15]C=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.BrBr.[C:25]([O-])(=O)[CH3:26].[Na+].C([O-])(=O)C.[NH4+:34].[NH4+:35].[OH-:36]>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:34]=[C:25]([CH3:26])[O:36][C:9]=2[C:11]2[CH:16]=[CH:15][N:35]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 14923Ammonium HydroxideHCID 24408BromineHCID 517045Sodium AcetateHCID 517165Ammonium AcetateHCID 21704185HCID 21704185, compound

Product 1

HCID 15540504HCID 15540504, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluorophenyl-2-(4-pyridyl)acetophenone [See PCT/US93/00674, Adams et al., published as WO93/14081](0.167 g, 0.76 mmol) in CH2Cl2 (5 mL) was added bromine (7.8 mL, 0.78 mmol; 0.1M soln in CH2Cl2). After stirring at room temperature for 30 min, the solvent was removed in vacuo and the solid was taken up in glacial acetic acid (10 mL). Sodium acetate (0.192 g, 2.34 mmol) and ammonium acetate (0.301 g, 3.9 mmol) were added and the reaction mixture was heated at reflux for 19 h. After cooling, the mixture was poured into H2O, neutralized with conc. NH4OH, then extracted exhaustively with CH2Cl2. The combined organic layers were washed with sat'd NaCl and dried over MgSO4. Evaporation of solvent provided a yellow solid which was purified by flash chromatography, eluting with 100% CHCl3. The title compound was obtained as a yellow waxy solid (0.067 g): ESMS (m/z): 255 (M++H).

Workup

  1. customthe solvent was removed in vacuo
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 19 h
  4. temperatureAfter cooling
  5. extractionextracted exhaustively with CH2Cl2
  6. washThe combined organic layers were washed with sat'd NaCl
  7. dry with materialdried over MgSO4
  8. customEvaporation of solvent
  9. customprovided a yellow solid which
  10. customwas purified by flash chromatography
  11. washeluting with 100% CHCl3

Sources & evidence

ORD record
ord-c3ee76548d14430fb09a1b3072981145
Source dataset
uspto-grants-2001_09
Patent number
US06288062B1

Reaction notes

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