1-Butanol → HCID 71255395, compound

HRID 540306Notes

Reaction equation

HRID 540306 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=2)[N:3]=1.[Br:14][C:15]1[CH:16]=[CH:17][C:18]2[CH2:24][NH:23][CH2:22][CH2:21][CH2:20][C:19]=2[CH:25]=1.C(O)CCC>C(OCC)(=O)C>[Br:14][C:15]1[CH:16]=[CH:17][C:18]2[CH2:24][N:23]([C:2]3[CH:11]=[C:10]([Cl:12])[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=4)[N:3]=3)[CH2:22][CH2:21][CH2:20][C:19]=2[CH:25]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 187966912,4,6-TrichloroquinolineHCID 533970047-Bromo-2,3,4,5-tetrahydro-1H-2-benzazepine

Product 1

HCID 71255395HCID 71255395, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

The mixture of 2,4,6-trichloroquinoline (300 mg, 1.29 mmol), 7-bromo-2,3,4,5-tetrahydro-1H-2-benzazepine (291 mg, 1.29 mmol) and n-butanol (3 mL) was heated with stirring in a 10 mL microwave process vial for 1 hour at 160° C. under microwave irradiation. The mixture was cooled to room temperature and diluted with ethyl acetate (10 mL), and then washed with water (10 mL). The organic layer was dried over sodium sulfate and evaporated to give a residue which was purified by column chromatography on silica gel to give 222 mg of product as a white solid (yield was 41%). MS obsd. (ESI+) [(M+H)+] 421.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with water (10 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated
  6. customto give a residue which
  7. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bd55cadd7eb14d978f57d74e12359879
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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