6-Chloro-4-oxo-1,2,3,4-tetrahydrocarbazole → HCID 178513134, compound

HRID 966068Notes

Reaction equation

HRID 966068 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][C:6](=O)[C:5]2=1.C(=O)(O)O.[NH2:20][NH:21][C:22]([NH2:24])=[NH:23]>C(O)(C)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][C:6](=[N:20][NH:21][C:22](=[NH:23])[NH2:24])[C:5]2=1

Participants

5

Reactant 2

HCID 3357036-Chloro-4-oxo-1,2,3,4-tetrahydrocarbazoleHCID 178513185HCID 178513185, compound

Product 1

HCID 178513134HCID 178513134, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 6-chloro-4-oxo-1,2,3,4-tetrahydrocarbazole (21.9 mg, 0.1 mmol) in isopropanol and concentrated HCl (50 μL) is treated with aminoguanidine bicarbonate (20.4 μg, 0.15 mmol), heated at 80° C. for 4 h, cooled to room temperature and concentrated in vacuo. The resultant residue is purified by HPLC to give the title compound, 15.8 mg (49% yield), identified by mass spectral and HPLC analyses, (M+H) 276; retention time 3.72 min.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue is purified by HPLC

Sources & evidence

ORD record
ord-2e73cb7cb0954efe8e1492f7b2a9d7e5
Source dataset
uspto-grants-2005_10
Patent number
US06951881B2

Reaction notes

Loading…