Water → 3-Dimethylaminomethylene-2-oxo-2,3-dihydro-1h-indole-5-sulfonic acid

HRID 878792Notes

Reaction equation

HRID 878792 reaction equation
C(N[S:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11]2)(=[O:7])=[O:6])(C)C.[CH3:18][N:19]([CH:21](OC)OC)[CH3:20].[OH2:26]>CN(C=O)C>[CH3:18][N:19]([CH:21]=[C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([S:5]([OH:6])(=[O:7])=[O:26])[CH:9]=2)[NH:13][C:12]1=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 219156105-Isopropylaminosulfonyl-2-oxindole

Product 1

HCID 909680093-Dimethylaminomethylene-2-oxo-2,3-dihydro-1h-indole-5-sulfonic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of rpm281 (0.180 g, 0.708 mmol) and N,N-dimethylformamidedimethylacetal (0.125 g, 0.85 mmol, 1.2 eq) in DMF (2 ml) was stirred for 1 h at room temperature. Water (7 ml) was added and the product extracted with ethyl acetate (3×10 ml). The organic extracts were collected, dried over Na2SO4 and the solvent evaporated under reduced pressure to give a yellow solid, which was used in the next step without further purification.

Workup

  1. extractionthe product extracted with ethyl acetate (3×10 ml)
  2. customThe organic extracts were collected
  3. dry with materialdried over Na2SO4
  4. customthe solvent evaporated under reduced pressure
  5. customto give a yellow solid, which
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-37fdaf6ffeb54a2ea737b7c242726551
Source dataset
uspto-grants-2015_03
Patent number
US08987474B2

Reaction notes

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