Lithium Hydroxide → 6-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid

HRID 2410657Notes

Reaction equation

HRID 2410657 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15](=[O:17])[NH2:16])[CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([C:18]([O:20]CC)=[O:19])[CH2:6][C:5]2=1.[Li+].[OH-]>C1COCC1.CCO.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15](=[O:17])[NH2:16])[CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([C:18]([OH:20])=[O:19])[CH2:6][C:5]2=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66605138ethyl 6-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

Product 1

HCID 666051346-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

A suspension of ethyl 6-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate (0.9 g, 2.464 mmol) and LiOH (0.177 g, 7.39 mmol) in THF/EtOH/H2O (3/1/1) (25 mL) was stirred at room temperature for 72 hours The reaction mixture was concentrated and the residue was dissolved in water. Aqueous 1M HCl was added to this solution until pH=5 whereupon a light yellow solid precipitated. The solid was collected by filtration, washed with water, air-dried and used as such in the next reaction. LCMS: RT=0.96 min, m/z (M+H) 337.0/339.0.

Workup

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in water
  3. additionAqueous 1M HCl was added to this solution until pH=5 whereupon a light yellow solid
  4. customprecipitated
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customair-dried
  8. customsuch in the next reaction

Sources & evidence

ORD record
ord-efd529304e8644b8a2b2e11c85d67d77
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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