Lithium Hydroxide → 3-[1-(Benzenesulfonyl)indol-5-YL]prop-2-enoic acid

HRID 84181Notes

Reaction equation

HRID 84181 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:26])[CH:6]=[CH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH:12]=[CH:11]2>O1CCOCC1>[C:20]1([S:17]([N:13]2[C:14]3[C:10](=[CH:9][C:8]([CH:7]=[CH:6][C:5]([OH:26])=[O:4])=[CH:16][CH:15]=3)[CH:11]=[CH:12]2)(=[O:19])=[O:18])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 673571463-(1-benzenesulfonyl-1H-indol-5-yl)-acrylic acid methyl ester

Product 1

HCID 674343693-[1-(Benzenesulfonyl)indol-5-YL]prop-2-enoic acidYield 89.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

1M LiOH aqueous solution (11.72 ml, 11.72 mmol) was added to a solution of 7 (2.00 g, 5.86 mmol) in dioxane (20 mL). The reaction mixture was stirred at 40° C. overnight and was then concentrated under reduced pressure. The residue was dissolved in water. Then concentrated HCl was added to the solution to reach acidic pH to give the precipitation, which was dried by vacuum to afford 8 (1.72 g) as a white solid. 1H NMR (500 MHz, CDCl3): δ6.39 (d, J=16.1 Hz, 1H), 6.71 (d, J=3.6 Hz, 1H), 7.45-7.48 (m, 2H), 7.52 (dd, J=8.7, 1.4 Hz, 1H), 7.55-7.58 (m, 1H), 7.61 (d, J=3.7 Hz, 1H), 7.67-7.72 (m, 2H), 7.89 (d, J=8.9 Hz, 2H), 7.96 (d, J=8.7 Hz, 1H).

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. additionThen concentrated HCl was added to the solution
  4. customto give
  5. customthe precipitation, which
  6. customwas dried by vacuum

Sources & evidence

ORD record
ord-f347979756c34c10a3c522cb75bdc48f
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Reaction notes

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