Sulfuric Acid → HCID 14502056, compound

HRID 231863Notes

Reaction equation

HRID 231863 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][N:6]1[CH:14]([C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:24])[CH3:2].S(=O)(=O)(O)O.[C:32](=O)([O-])O.[Na+]>CO>[CH2:25]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[CH:14]([C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([O:19][CH3:32])=[O:18])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:24])[CH3:26]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 14502055HCID 14502055, compound

Product 1

HCID 14502056HCID 14502056, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.53 g of Compound 27 in 5 ml of methyl alcohol was added 0.2 ml of conc. sulfuric acid. After heating at reflux for 2 hours, pH was adjusted to 7 with sodium hydrogencarbonate. The mixture was concentrated under reduced pressure. After 30 ml of water and 30 ml of methylene chloride were added to the residue, pH was adjusted to 12 with 10N-sodium hydroxide solution. After shaking, the aqueous layer was discarded and the organic layer was washed with saturated aqueous sodium chloride solution. After drying over anhydrous sodium sulfate, the organic layer was concentrated under reduced pressure to give 0.14 g of methyl 2-[2-(2-diethylaminoethyl)isoindolin-1-on-3-yl]benzoate (Compound 28).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionAfter 30 ml of water and 30 ml of methylene chloride were added to the residue, pH
  5. washthe organic layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-84111d5b855f4ea081570ab6bfa6ed99
Source dataset
uspto-grants-1989_07
Patent number
US04849441

Reaction notes

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