Hydrochloric Acid → 6-nitro-1h-indole-3-carboxylic acid

HRID 1517953Notes

Reaction equation

HRID 1517953 reaction equation
FC(F)(F)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].[OH-:19].[Na+].Cl>O>[N+:14]([C:10]1[CH:9]=[C:8]2[C:13]([C:5]([C:3]([OH:4])=[O:19])=[CH:6][NH:7]2)=[CH:12][CH:11]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22497236HCID 22497236, compound

Product 1

HCID 2560996-nitro-1h-indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3.7 g 2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)-ethanone are combined with 20 ml of a 40% sodium hydroxide solution solution and refluxed for 4 hours. After cooling to 0° C. the mixture is diluted with a little water and adjusted to pH 1 by the careful addition of concentrated hydrochloric acid. The precipitated solid is suction filtered and dissolved in dichloromethane/methanol 10:1. After drying with magnesium sulphate the solvents are eliminated in vacuo and the residue is extracted from diethyl ether.

Workup

  1. temperaturerefluxed for 4 hours
  2. filtrationfiltered
  3. dissolutiondissolved in dichloromethane/methanol 10:1
  4. dry with materialAfter drying with magnesium sulphate the solvents
  5. extractionthe residue is extracted from diethyl ether

Sources & evidence

ORD record
ord-96a56a4b4d4c48e88e6063c919c810b8
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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