Sodium Chloride → HCID 18972164, compound

HRID 2395359Notes

Reaction equation

HRID 2395359 reaction equation
[OH:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:7]([CH3:14])[C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.[H-].[Na+].[CH3:22]I.[Cl-].[Na+]>O1CCCC1>[CH3:22][O:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:7]([CH3:14])[C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18972186HCID 18972186, compound

Product 1

HCID 18972164HCID 18972164, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1,3,4,5-tetrahydro-5-hydroxy-1-methyl-benz[cd]indole-2-carboxylate (0.25 g, 0.96 mmol) was added to a suspension of 60% sodium hydride (0.039 g, 0.96 mmol) in tetrahydrofuran (10 ml), followed by stirring at room temperature for 20 minutes. After the reaction mixture was cooled to 0°-5° C., methyl iodide (0.27 g, 1.93 mmol) was added thereto and the resulting mixture was stirred at 0°-5° C. for 1 hour and then at room temperature for 2.5 hours. The reaction mixture was poured into a 5% aqueous sodium chloride solution, followed by extraction with ethyl acetate (twice). The extract solution was washed twice with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98) to obtain ethyl 1,3,4,5-tetrahydro-5-methoxy-1-methyl-benz[cd]indole-2-carboxylate (0.16 g).

Workup

  1. temperatureAfter the reaction mixture was cooled to 0°-5° C.
  2. stirringthe resulting mixture was stirred at 0°-5° C. for 1 hour
  3. waitat room temperature for 2.5 hours
  4. extractionfollowed by extraction with ethyl acetate (twice)
  5. washThe extract solution was washed twice with a 5% aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98)

Sources & evidence

ORD record
ord-f8c857dd06bf4ccd8508420f3f772caa
Source dataset
uspto-grants-1998_09
Patent number
US05814654

Reaction notes

Loading…