Ammonium Chloride → HCID 58294586, compound

HRID 520994Notes

Reaction equation

HRID 520994 reaction equation
[Br-].[CH2:2]([Zn+])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:11]1[CH:24]=[CH:23][C:14]2[C:15]3[CH:16]=[CH:17][CH:18]=[N:19][C:20]=3[CH2:21][CH2:22][C:13]=2[CH:12]=1.[NH4+].[Cl-]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:2]([C:11]1[CH:24]=[CH:23][C:14]2[C:15]3[CH:16]=[CH:17][CH:18]=[N:19][C:20]=3[CH2:21][CH2:22][C:13]=2[CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58294389HCID 58294389, compoundHCID 178419772HCID 178419772, compound

Product 1

HCID 58294586HCID 58294586, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Benzylzinc bromide (0.5 mol/L in tetrahydrofuran, 7.7 mL) is added to a flask charged with a stir bar, tetrakis(triphenylphosphine)palladium(0) (53 mg), and 8-bromo-5,6-dihydro-benzo[f]quinoline (0.20 g) and kept under argon atmosphere at room temperature. The resulting solution is heated to reflux temperature and stirred at this temperature for 6 h. After cooling the solution to room temperature, aqueous NH4Cl solution is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine and dried (Na2SO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1) to afford the title compound as an oil. Yield: 0.17 g (81% of theory); LC (method 1): tR=3.08 min; Mass spectrum (ESI+): m/z=272 [M+H]+.

Workup

  1. additioncharged with a stir bar
  2. customkept under argon atmosphere at room temperature
  3. temperatureThe resulting solution is heated
  4. temperatureto reflux temperature
  5. extractionthe resulting mixture is extracted with ethyl acetate
  6. washThe combined extracts are washed with brine
  7. dry with materialdried (Na2SO4)
  8. customThe solvent is evaporated
  9. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1)

Sources & evidence

ORD record
ord-17d9be26d9e34c358178b1500d78e755
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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