Acetic Acid → 6-Hydroxy-1,2,3,4-tetrahydro-beta-carboline

HRID 6740

Reaction equation

HRID 6740 reaction equation
[C:1](O)(=O)C.Cl.[NH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[NH:11][CH:10]=1.C(=O)C>CO>[CH2:1]1[C:10]2[NH:11][C:12]3[C:17](=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[C:9]=2[CH2:8][CH2:7][NH:6]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 160436Serotonin Hydrochloride

Product 1

HCID 1599596-Hydroxy-1,2,3,4-tetrahydro-beta-carboline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

Acetic acid was added dropwise to a solution of 3-(2-amino-ethyl)-1H-indol-5-ol hydrochloride (200 mg) in 7 mL of methanol until the pH=4. Acetaldehyde (0.2 mL) was added and the mixture was heated at 75° C. in a sealed tube for 1 h. The tube was cooled to rt and unsealed. The solvent was evaporated yielding 160 mg of 2,3,4,9-tetrahydro-1H-β-carbolin-6-ol.

Workup

  1. temperatureThe tube was cooled to rt
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ec54e13d81204fff901de7e6692aa8ad
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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