Hydrochloric Acid → 7-Chloro-beta-carboline

HRID 1795093Notes

Reaction equation

HRID 1795093 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:13][C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:5]=2[CH:6]=1.Cl.[Cl:15]N1C(=O)CCC1=O.C([O-])([O-])=O.[K+].[K+]>O>[Cl:15][C:2]1[CH:3]=[C:4]2[C:5]([C:7]3[CH:8]=[CH:9][N:10]=[CH:11][C:12]=3[NH:13]2)=[CH:6][CH:1]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 31398ChlorosuccinimideHCID 64961Beta-Carboline

Product 1

HCID 221852817-Chloro-beta-carbolineYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of norharmane (2.0 g, 11.9 mmol) in water (89 ml) and 1M aqueous HCl (29.8 ml, 29.8 mmol) was added N-chlorosuccinimide (3.17 g, 23.8 mmol) portionwise. The resulting solution was stirred at RT for 6 h, and then at 0° C. to 5° C. for 12 h. The reaction was diluted with water (100 ml) and basified cautiously with solid K2CO3 (4.3 g). After stirring at RT for 1 h, the product was collected and washed with water. The crude product was refluxed in chloroform for 1 h and filtered after cooling to 15° C. to provide 2.05 g of 7-chloro-β-carboline.

Workup

  1. waitat 0° C. to 5° C. for 12 h
  2. stirringAfter stirring at RT for 1 h
  3. customthe product was collected
  4. washwashed with water
  5. temperatureThe crude product was refluxed in chloroform for 1 h
  6. filtrationfiltered
  7. temperatureafter cooling to 15° C.

Sources & evidence

ORD record
ord-632c729aa18b4a77b435c178b8992606
Source dataset
uspto-grants-2006_04
Patent number
US07026331B2

Reaction notes

Loading…