Ethanol → ethyl (3S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate

HRID 1249097Notes

Reaction equation

HRID 1249097 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@@H:3]([C:14]([OH:16])=[O:15])[NH:2]1.O=S(Cl)Cl.[CH2:21](O)[CH3:22]>>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@@H:3]([C:14]([O:16][CH2:21][CH3:22])=[O:15])[NH:2]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 449440(3S)-1H,2H,3H,4H,9H-pyrido(3,4-b)indole-3-carboxylic acid

Product 1

HCID 1079579ethyl (3S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylateYield 68%

Procedure

(3S)-1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid (32.5 g) is suspended in ethanol (500 ml) and thereto is added dropwise SOCl2 (13.0 ml) at 0° C. The mixture is refluxed for 8 hours and then distilled to remove the solvent. The residue is dissolved in water and is made alkaline with NH4OH and extracted with ethyl acetate. The extract is dried and distilled to remove the solvent. The residue is recrystallized from ethyl acetate-isopropyl ether to give the title compound (24.86 g, 68%) as colorless needles, m.p. 135°-137° C.

Workup

  1. temperatureThe mixture is refluxed for 8 hours
  2. distillationdistilled
  3. customto remove the solvent
  4. dissolutionThe residue is dissolved in water
  5. extractionextracted with ethyl acetate
  6. customThe extract is dried
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-99467aaffde646e5af823df7072e2424
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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