Chlorosuccinimide → HCID 22185276, compound

HRID 1168735Notes

Reaction equation

HRID 1168735 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:15]=1[NH:14][C:13]1[CH:12]=[N:11][CH:10]=[CH:9][C:8]2=1.[Cl:16]N1C(=O)CCC1=O>C1COCC1>[Cl:16][C:4]1[C:3]([O:2][CH3:1])=[C:15]2[C:7]([C:8]3[CH:9]=[CH:10][N:11]=[CH:12][C:13]=3[NH:14]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 221852248-Methoxy-9H-pyrido[3,4-b]indole

Product 1

HCID 22185276HCID 22185276, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 8-methoxy-β-carboline (1.0 g, 5 mmol) in THF (100 ml) was added N-chlorosuccinimide (0.70 g, 5.2 mmol). The reaction was stirred at RT for 4 h before concentrating and washing the residue with 1:1:1 mixture of 10% Na2CO3, hexane, and EtOAc (400 ml). The resulting residue was triturated with xylenes to provide 677 mg of 7-chloro-8-methoxy-β-carboline. A solution of 7-chloro-8-methoxy-β-carboline (677 mg, 2.9 mmol) in trifluoroacetic acid (10 ml) was treated with NaNO3 (260 mg, 3.06 mmol). The reaction was stirred for 3 h at RT and then concentrated. The crude product was chromatographed on silica eluting with a 5% to 10% methanol in chloroform gradient to provide 463 mg of 7-chloro-8-methoxy-9-nitro-β-carboline.

Workup

  1. concentrationbefore concentrating
  2. washwashing the residue
  3. additionwith 1:1:1 mixture of 10% Na2CO3, hexane, and EtOAc (400 ml)
  4. customThe resulting residue was triturated with xylenes

Sources & evidence

ORD record
ord-8416990928414304a3c3ce6792d7d1af
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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