Sodium Bicarbonate → 4-(5-Cyano-1-methyl-3-indolyl)cyclohexanone

HRID 1872835Notes

Reaction equation

HRID 1872835 reaction equation
C1O[C:4]2([CH2:9][CH2:8][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[N:20])[CH:17]=4)[N:12]([CH3:21])[CH:11]=3)[CH2:6][CH2:5]2)[O:3]C1.C(=O)(O)[O-].[Na+]>O1CCCC1.Cl>[C:19]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:21])[CH:11]=[C:10]2[CH:7]1[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]1)#[N:20]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 184140773-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-cyano-1-methyl-indole

Product 1

HCID 154812824-(5-Cyano-1-methyl-3-indolyl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 18422008HCl tetrahydrofuranSolvent

Procedure

A solution of 4-(5-cyano-1-methyl-3-indolyl)-cyclohexanone ethylene ketal (5.5 g) in 150 ml (1:1) tetrahydrofuran-hydrochloric acid (1N) was allowed to stir at room temperature for 16 hours, then to above solution sodium bicarbonate (4.49 g) was added. The mixture was extracted with methylene chloride (3×100 ml) and washed with brine (3×150 ml). The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was removed to afford a light brown solid which was boiled in ethyl acetate-hexanes (1:1). The mixture was cooled to room temperature and solid was collected and dried under vacuum (2.06 g): mp 150-152° C.

Workup

  1. extractionThe mixture was extracted with methylene chloride (3×100 ml)
  2. washwashed with brine (3×150 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed
  6. customto afford a light brown solid which
  7. temperatureThe mixture was cooled to room temperature
  8. customsolid was collected
  9. customdried under vacuum (2.06 g)

Sources & evidence

ORD record
ord-b42ee60872ad44e6adda3f6d782ec58c
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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