Pyridine → 6-Bromo-4-methyl-beta-carbolin-3-carboxylic acid ethyl ester

HRID 1757972Notes

Reaction equation

HRID 1757972 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].N1C=CC=CC=1.[Br:26]Br>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([Br:26])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 12795657HCID 12795657, compound

Product 1

HCID 130373286-Bromo-4-methyl-beta-carbolin-3-carboxylic acid ethyl esterYield 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

0.5 g of 4-methyl-β-carbolin-3-carboxylic acid ethyl ester (melting point 235°-239° C.) is dissolved in 25 ml of chloroform and 1.7 ml of pyridine and a solution of 1 ml of bromine in 21 ml of chloroform is added dropwise thereto at 0° C. After standing for one hour while cooling with ice and after dilution with 50 ml of the methylene chloride, the mixture is extracted by washing with sodium thiosulphate solution, dilute aqueous ammonia solution and water. After drying with sodium sulphate, filtering off and distilling off the solvent in vacuo, 6-bromo-4-methyl-β-carbolin-3-carboxylic acid ethyl ester is obtained in 38% yield, Melting point 231°-232° C. (from acetone).

Workup

  1. customat 0° C
  2. temperaturewhile cooling with ice
  3. extractionafter dilution with 50 ml of the methylene chloride, the mixture is extracted
  4. washby washing with sodium thiosulphate solution, dilute aqueous ammonia solution and water
  5. dry with materialAfter drying with sodium sulphate
  6. filtrationfiltering off
  7. distillationdistilling off the solvent in vacuo

Sources & evidence

ORD record
ord-0fdeb74e1d7942e3bc2ae356577bf762
Source dataset
uspto-grants-1983_02
Patent number
US04371536

Reaction notes

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