Water → 3-Ethoxy-9H-pyrido[3,4-b]indole

HRID 569033Notes

Reaction equation

HRID 569033 reaction equation
[CH2:1]([O:6]N=O)[CH2:2]C(C)C.N[C:10]1[N:11]=[CH:12][C:13]2[NH:14][C:15]3[C:20]([C:21]=2[CH:22]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3.O.C(=O)(O)[O-].[Na+]>C(O)C.S(=O)(=O)(O)O>[CH2:1]([O:6][C:10]1[N:11]=[CH:12][C:13]2[NH:14][C:15]3[C:20]([C:21]=2[CH:22]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8053Isoamyl NitriteHCID 1195373-AminonorharmanHCID 516892Sodium Bicarbonate

Product 1

HCID 1244773-Ethoxy-9H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

1 ml of isoamylnitrite is added to a suspension of 1 g of 3-amino-β-carboline in 100 ml of ethanol and 2 ml of concentrated sulfuric acid. The mixture is stirred at room temperature for an hour and then refluxed for an hour. As a result, a clear solution is obtained. After cooling, it is poured into a mixture of 100 ml of water and 100 ml of saturated sodium bicarbonate solution. It is extracted three times with 100 ml of ether each time and the evaporation residue of the combined ether extracts is chromatographed (silica gel, methanol/chloroform=95:5) and recrystallized from hexane. Yield: 0.3 g of 3-ethoxy-β-carboline with a melting point of 130°-133° C.

Workup

  1. temperaturerefluxed for an hour
  2. customAs a result, a clear solution is obtained
  3. temperatureAfter cooling
  4. extractionIt is extracted three times with 100 ml of ether each time
  5. customthe evaporation residue of the combined ether extracts is chromatographed (silica gel, methanol/chloroform=95:5)
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-f019864e759b4eb5972d5bfab95e73c1
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Reaction notes

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