Ethanol → HCID 18972187, compound

HRID 2395358Notes

Reaction equation

HRID 2395358 reaction equation
[O:1]=[C:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.[BH4-].[Na+].C(O)C.[Cl-].[Na+]>O1CCCC1>[OH:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 12377168HCID 12377168, compound

Product 1

HCID 18972187HCID 18972187, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 1,3,4,5-tetrahydro-5-oxo-benz[cd]indole-2-carboxylate (0.40 g, 1.64 mmol), sodium borohydride (0.062 g, 1.64 mmol), ethanol (2 ml) and tetrahydrofuran (8 ml) was stirred at 0°-5° C. for 1.5 hours. The reaction mixture was poured into a 5% aqueous sodium chloride solution, followed by extraction with ethyl acetate (three times). 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=15/85) to obtain ethyl 1,3,4,5-tetrahydro-5-hydroxy-benz[cd]indole-2-carboxylate (0.40 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate (three times)
  2. washThe extract solution was washed twice with a 5% aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=15/85)

Sources & evidence

ORD record
ord-1af90e1ecbfd4ba5af99d98128483c8b
Source dataset
uspto-grants-1998_09
Patent number
US05814654

Reaction notes

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