Lithium Hydroxide → HCID 25744650, compound

HRID 84191Notes

Reaction equation

HRID 84191 reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH2:11][CH2:10]2)=[O:6]>O1CCOCC1>[C:19]1([S:16]([N:12]2[C:13]3[C:9](=[CH:8][C:7]([C:5]([OH:6])=[O:4])=[CH:15][CH:14]=3)[CH2:10][CH2:11]2)(=[O:18])=[O:17])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 31756086Methyl 1-(Phenylsulfonyl)indoline-5-carboxylate

Product 1

HCID 25744650HCID 25744650, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

1M LiOH aqueous solution (2.4 ml, 2.40 mmol) was added to a solution of 11 (0.38 g, 1.20 mmol) in dioxane (15 mL). The reaction mixture was stirred at 40° C. overnight and then 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 16 (0.34 g). 1H NMR (500 MHz, CD3OD): δ 2.97 (t, J=8.6 Hz, 2H), 3.99 (t, J=8.6 Hz, 2H), 7.51-7.54 (m, 2H), 7.61-7.64 (m, 2H), 7.74 (s, 1H), 7.84-7.88 (m, 3H).

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-b7a24551a1f34319a5084d47e707ac02
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Reaction notes

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