Chlorosuccinimide → HCID 67165350, compound

HRID 552221Notes

Reaction equation

HRID 552221 reaction equation
[CH3:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=[N:4][CH:3]=1.C1C(=O)N([Cl:22])C(=O)C1.C(=O)(O)[O-].[Na+]>Cl>[Cl:22][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[C:14]2=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 593375704-Methyl-9H-beta-carboline

Product 1

HCID 67165350HCID 67165350, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-methyl-9H-β-carboline (97 mg, 0.532 mmol) was dissolved in HCl (1N, 4 ml) and stirred at RT. NCS (85 mg, 0.637 mmol) was added thereto and the reaction mixture was stirred for 5 hr. Saturated sodium bicarbonate solution (20 ml) was added thereto and the reaction mixture was extracted twice with EtOAc (100 ml). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give 6-chloro-4-methyl-9H-β-carboline (108 mg) as an oil. 1H-NMR (300 MHz, DMSO-d6): δ 8.67 (s, 1); 8.19 (s, 1); 8.11 (s, 1); 7.57-7.54 (m, 2); 2.82 (s, 3). NH4OAc standard conditions. DAD Rf=2.48 min. M+H=217.

Workup

  1. stirringthe reaction mixture was stirred for 5 hr
  2. extractionthe reaction mixture was extracted twice with EtOAc (100 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2f34d6c6f4414743b69ce1c5114d9ff5
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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