Sodium Chloride → HCID 20203546, compound

HRID 978727Notes

Reaction equation

HRID 978727 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:18])=[C:8]3[C:15](=[N:16]O)[CH2:14][CH2:13][CH2:12][N:9]32)=[CH:5][CH:4]=1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:18])=[C:8]3[CH:15]([NH2:16])[CH2:14][CH2:13][CH2:12][N:9]32)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 86741128HCID 86741128, compound

Product 1

HCID 20203546HCID 20203546, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 6,7,8,9-tetrahydro-3-methoxy-10-methylpyrido[1,2-a]indol-9-one oxime (2.2 g, 9 mmol) in ethanol (50 mL) containing 10% sodium hydroxide (36 mL) was treated with Raney alloy (3.15 g) at 35° C. over 20 minutes. The reaction mixture was stirred at 45° C. for 18 hours, then poured into ice water (100 mL), saturated with sodium chloride. The product was extracted with ether (3×75 mL), dried and evaporated. The residue was dissolved in toluene (30 mL), and extracted with 3% hydrochloric acid (50 mL). The aqueous layer was separated, and basified with 50% sodium hydroxide upon cooling. The product was extracted with chloroform, dried over MgSO4, filtered, and evaporated. The dark oily residue was chromatographed on silica gel (50 g). Elution with chloroform afforded 1.87 g (91%) of the desired amine as an amber oil.

Workup

  1. additionwas treated with Raney alloy (3.15 g) at 35° C. over 20 minutes
  2. extractionThe product was extracted with ether (3×75 mL)
  3. customdried
  4. customevaporated
  5. dissolutionThe residue was dissolved in toluene (30 mL)
  6. extractionextracted with 3% hydrochloric acid (50 mL)
  7. customThe aqueous layer was separated
  8. temperatureupon cooling
  9. extractionThe product was extracted with chloroform
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated
  13. customThe dark oily residue was chromatographed on silica gel (50 g)
  14. washElution with chloroform

Sources & evidence

ORD record
ord-7ccd020368a8422791c34e440438a90a
Source dataset
uspto-grants-1987_05
Patent number
US04665183

Reaction notes

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