Lithium hydroxide, monohydrate → 5H-[1,3]dioxolo[4,5-f]indole-6-carboxylic acid

HRID 62653Notes

Reaction equation

HRID 62653 reaction equation
[O:1]1[C:5]2=[CH:6][C:7]3[CH:8]=[C:9]([C:13]([O:15]CC)=[O:14])[NH:10][C:11]=3[CH:12]=[C:4]2[O:3][CH2:2]1.O[Li].O>C(O)C>[O:1]1[C:5]2=[CH:6][C:7]3[CH:8]=[C:9]([C:13]([OH:15])=[O:14])[NH:10][C:11]=3[CH:12]=[C:4]2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10513792Ethyl 5H-[1,3]dioxolo[4,5-f]indole-6-carboxylate

Product 1

HCID 9073915H-[1,3]dioxolo[4,5-f]indole-6-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 5H-[1,3]dioxolo[4,5-f]indole-6-carboxylate (I-4b: 0.4 g, 1.716 mmol) in ethanol (8 mL) was added LiOH.H2O (0.144 g, 3.433 mmol) and refluxed for 16 h. The solvent was evaporated under reduced pressure and the residue was dissolved in water (10 mL). The aqueous layer was acidified with 10% aq. HCl solution to pH 6.0, precipitated solid was filtered, residue was washed with water and dried under vacuum to afford 0.3 g (86%) of 5H-[1,3]dioxolo[4,5-f]indole-6-carboxylic acid (I-4c) as an off-white solid.

Workup

  1. temperaturerefluxed for 16 h
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in water (10 mL)
  4. customprecipitated solid
  5. filtrationwas filtered
  6. washresidue was washed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f21ed9fa3d754708bfa80aee6037189b
Source dataset
uspto-grants-2016_09
Patent number
US09447039B2

Reaction notes

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