Hydrogen Bromide → HCID 13315122, compound

HRID 569032Notes

Reaction equation

HRID 569032 reaction equation
N[C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.N([O-])=O.[Na+].[BrH:19]>>[Br:19][C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

4

Reactant 3

HCID 260Hydrogen Bromide2×HCID 1195373-AminonorharmanHCID 23668193Sodium Nitrite

Product 1

HCID 13315122HCID 13315122, compound

Procedure

2 g of 3-amino-β-carboline, suspended in 25 ml of 48% hydrobromic acid, are mixed with 6 ml of a 2-molar sodium nitrite solution at 0°-5° C. The mixture is added at 0°-5° C. to a solution of 2.1 g of copper-I-bromide in 20 ml of 24% hydrobromic acid. The reaction mixture is heated briefly in a steam bath and then repeatedly extracted with a mixture consisting of 9 parts of ethyl acetate and one part of ethane. The combined extracts are evaporated, the residue chromatographed (silica gel, methylene chloride/methanol=19:1). The main fraction crystallizes on treatment with ethyl acetate. Yield: 0.5 g of 3-bromo-β-carboline; melting point: 300° C.

Workup

  1. temperatureThe reaction mixture is heated briefly in a steam bath
  2. extractionrepeatedly extracted with a mixture
  3. customThe combined extracts are evaporated
  4. customthe residue chromatographed (silica gel, methylene chloride/methanol=19:1)
  5. customThe main fraction crystallizes on treatment with ethyl acetate

Sources & evidence

ORD record
ord-9e8cfa096ae04efcadd3be326dad5fce
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Reaction notes

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