Potassium Hydroxide → 5-Bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic Acid

HRID 342798Notes

Reaction equation

HRID 342798 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=[O:5])C.[OH-].[K+]>C(O)C.O>[Br:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)[C:6]([C:4]([OH:5])=[O:3])=[CH:14]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 543953975-bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 540736965-Bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic AcidYield 77.6%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a stirred solution of 5-bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic acid ethyl ester (2.3 g, 5.7 mmol) in ethanol/water (2:1, 45 ml) at room temperature was added potassium hydroxide (0.96 g, 17.1 mmol). The solution was warmed to reflux for about 3 hours, cooled, and most of the ethanol was removed under reduced pressure. To the residue was added water, 0.5N sodium hydroxide and methylene chloride, and the two-phase mixture was suction filtered to remove some insoluble material. The aqueous layer was acidified to pH 2 with 6N hydrochloric acid, and the precipitate was filtered off, washed with water, and air dried to afford the title compound, (1.66 g).

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux for about 3 hours
  3. temperaturecooled
  4. custommost of the ethanol was removed under reduced pressure
  5. additionTo the residue was added water, 0.5N sodium hydroxide and methylene chloride
  6. filtrationfiltered
  7. customto remove some insoluble material
  8. filtrationthe precipitate was filtered off
  9. washwashed with water, and air
  10. customdried

Sources & evidence

ORD record
ord-c50204e6030b4aedb10c4f8ecb9dcf0b
Source dataset
uspto-grants-1999_01
Patent number
US05859044

Reaction notes

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