Lithium Hydroxide → 3-[1-(Phenylsulfonyl)indolin-5-yl]acrylic Acid

HRID 84189Notes

Reaction equation

HRID 84189 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])[CH2:12][CH2:11]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)[CH2:11][CH2:12]2)(=[O:19])=[O:18])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 674341053-(1-Benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-acrylic acid methyl ester

Product 1

HCID 674346323-[1-(Phenylsulfonyl)indolin-5-yl]acrylic AcidYield 83.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

1M LiOH aqueous solution (1.16 ml, 1.16 mmol) was added to a solution of 14 (0.20 g, 0.58 mmol) in dioxane (15 mL). The reaction mixture was stirred at 40° C. overnight before it was concentrated under reduced pressure. The residue was dissolved in water and concentrated HCl was added up to acidic pH to give the precipitation, which was dried by vacuum to afford 15 (0.16 g). 1H NMR (500 MHz, CD3OD): δ 2.92 (t, J=8.5 Hz, 2H), 3.96 (t, J=8.5 Hz, 2H), 6.33 (d, J=15.9 Hz, 1H), 7.38 (s, 1H), 7.41 (d, J=8.5 Hz, 1H), 7.50-7.53 (m, 2H), 7.55 (d, J=16.1 Hz, 1H), 7.58-7.64 (m, 2H), 7.82 (d, J=7.6 Hz, 2H).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. additionconcentrated HCl was added up to acidic pH
  4. customto give
  5. customthe precipitation, which
  6. customwas dried by vacuum

Sources & evidence

ORD record
ord-5d0257ccef1945dbb5215fcb454a2487
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Reaction notes

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