Hydrochloric Acid → HCID 15941912, compound

HRID 2221140Notes

Reaction equation

HRID 2221140 reaction equation
[C:1]1([C:7]2[C:15]3[O:14][C:13]([CH2:16][N:17]4C(=O)C5C(=CC=CC=5)C4=O)=[CH:12][C:11]=3[CH:10]=[C:9]([Cl:28])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN.Cl>C(O)C.C(O)(C)C>[Cl:28][C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[O:14][C:13]([CH2:16][NH2:17])=[CH:12][C:11]=2[CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 69111905HCID 69111905, compound

Product 1

HCID 15941912HCID 15941912, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 2-[(7-phenyl-5-chloro-1-benzofuran-2-yl)methyl]-1H-isoindole-1,3(2H)-dione (0.382 g, 0.985 minol) in ethanol (10 mL) was added the methylamine (33% in ethanol, 20 mL) and the reaction mixture was heated to 70° C. and allowed to stir for 1 h. The reaction mixture was allowed to cool to room temperature and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed with water (2×20 mL), saturated aqueous sodium bicarbonate (20 mL), saturated aqueous sodium chloride (20 mL), dried (magnesium sulfate), and the solvent removed in vacuo. Purification by flash column chromatography (silica, 10% ammonium hydroxide in methanol:ethyl acetate 1:9) provided a colorless oil that was dissolved in isopropanol (2 mL) and hydrogen chloride (1.0 N in diethyl ether, 5 mL) was added. The resulting precipitate was filtered, washed (diethylether), and dried to afford 0.165 g (57%) of [(5-chloro-7-phenyl-1-benzofuran-2-yl)methyl]amine as a white solid. mp>225° C.

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  4. washwashed with water (2×20 mL), saturated aqueous sodium bicarbonate (20 mL), saturated aqueous sodium chloride (20 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent removed in vacuo
  7. customPurification by flash column chromatography (silica, 10% ammonium hydroxide in methanol:ethyl acetate 1:9)
  8. customprovided a colorless oil that
  9. filtrationThe resulting precipitate was filtered
  10. washwashed (diethylether)
  11. customdried

Sources & evidence

ORD record
ord-4e7312eeaa034d4fbed6a5a75929b720
Source dataset
uspto-grants-2008_05
Patent number
US07368477B2

Reaction notes

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