Dimethyl Sulfate → 1H-Pyrido(4,3-b)indol-1-one, 2,3,4,5-tetrahydro-5-methyl-

HRID 1614293Notes

Reaction equation

HRID 1614293 reaction equation
[CH3:1]OS(OC)(=O)=O.[C:8]1(=[O:21])[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10][NH:9]1.[OH-].[Na+]>CC(C)=O>[CH3:1][N:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[C:20]2[C:8](=[O:21])[NH:9][CH2:10][CH2:11][C:12]1=2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 156163232,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one

Product 1

HCID 117902131H-Pyrido(4,3-b)indol-1-one, 2,3,4,5-tetrahydro-5-methyl-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dimethylsulphate (2.28 ml) was added over 5 min to a stirred mixture of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (3 g), acetone (12 ml) and 20% w/v aqueous sodium hydroxide (9 ml) at ca. 50°. The mixture was heated at reflux for 10 min. Further sodium hydroxide (6 ml) was added and the mixture was heated at reflux for 5 min. On cooling a solid crystallised. Water (10 ml) was added and the mixture was filtered. The solid was washed with water (2×20 ml), and dried in vacuo 45° to give the title compound (3.16 g). The t.l.c. data for this material were consistent with those obtained for the product of Example 1.

Workup

  1. customat ca. 50°
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 10 min
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 5 min
  6. temperatureOn cooling a solid
  7. customcrystallised
  8. additionWater (10 ml) was added
  9. filtrationthe mixture was filtered
  10. washThe solid was washed with water (2×20 ml)
  11. customdried in vacuo 45°

Sources & evidence

ORD record
ord-1d535169c9444eb2a1ba59422b056a5d
Source dataset
uspto-grants-1993_03
Patent number
US05196534

Reaction notes

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