Nitric Acid → ethyl 6-nitro-9H-beta-carboline-3-carboxylate

HRID 1085445Notes

Reaction equation

HRID 1085445 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[CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>>[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[CH:18]=1)=[CH:15][C:14]([N+:19]([O-:21])=[O:20])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 105078Ethyl Beta-Carboline-3-Carboxylate

Product 1

HCID 13037332ethyl 6-nitro-9H-beta-carboline-3-carboxylateYield 55%

Procedure

1 g of β-carbolin-3-carboxylic acid ethyl ester is slowly introduced at room temperature into 20 ml of concentrated nitric acid (65%). After addition is complete, the solution is heated to 70°-75° C., whereupon a clear solution forms. After about 30 minutes, the solution becomes turbid. After a total stirring time of 1.5 hours at 70°-75° C., the solution is allowed to cool and the sediment is poured onto 100 g of ice. After filtering with suction, recrystallization from pyridine is carried out. 6-nitro-β-carbolin-3-carboxylic acid ethyl ester of melting point 320°-325° C. is isolated in 55% yield.

Workup

  1. additionAfter addition
  2. temperaturethe solution is heated to 70°-75° C., whereupon a clear solution forms
  3. customAfter a total stirring time of 1.5 hours
  4. customat 70°-75° C.
  5. temperatureto cool
  6. filtrationAfter filtering with suction, recrystallization from pyridine

Sources & evidence

ORD record
ord-ee839a7847fe4772a2fc851f691d31aa
Source dataset
uspto-grants-1991_04
Patent number
US05010077

Reaction notes

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