Sodium Hydroxide → HCID 10059787, compound

HRID 1109107Notes

Reaction equation

HRID 1109107 reaction equation
C[O:2][C:3]1[C:8]2[C@@H:9]3[C@H:13]([CH2:14][CH2:15][C:7]=2[CH:6]=[CH:5][CH:4]=1)[N:12]([CH2:16][CH2:17][CH3:18])[CH2:11][CH2:10]3.[OH-].[Na+].C([O-])(O)=O.[Na+]>Br>[CH2:16]([N:12]1[C@@H:13]2[C@@H:9]([C:8]3[C:3]([OH:2])=[CH:4][CH:5]=[CH:6][C:7]=3[CH2:15][CH2:14]2)[CH2:10][CH2:11]1)[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 10037522HCID 10037522, compound

Product 1

HCID 10059787HCID 10059787, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

8.58 g (0.035 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-9-methoxy-3-propyl-1H-benzo[e]indole were boiled under reflux for 4 hours in 0.5 l of 48 percent aqueous HBr. The mixture was poured into an ice-cold aqueous solution of 200 g (5 mol) of NaOH. Solid NaHCO3 was added thereto and the mixture was extracted three times with CH2Cl2. The combined organic phases were washed with saturated aqueous NaHCO3 and NaCl solutions, dried with Na2SO4, filtered and concentrated. The residue was chromatographed over silica gel with ethyl acetate. The product was crystallized in hexane. There were obtained 6.4 g (80%) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-propyl-1H-benzo[e]indol-9-ol as white crystals with m.p. 130°-132°.

Workup

  1. extractionthe mixture was extracted three times with CH2Cl2
  2. washThe combined organic phases were washed with saturated aqueous NaHCO3 and NaCl solutions
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed over silica gel with ethyl acetate
  7. customThe product was crystallized in hexane

Sources & evidence

ORD record
ord-19104a2c96454cd9a8d371b86e443e0f
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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