Hydrochloric Acid → HCID 67265769, compound

HRID 1685394Notes

Reaction equation

HRID 1685394 reaction equation
O.[CH2:2]([N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([O:21]C)=[O:20])[CH:15]=2)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1COCC1.Cl>CC(=O)OCC.CO>[CH2:2]([N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([OH:21])=[O:20])[CH:15]=2)[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 67266017HCID 67266017, compound2×

Product 1

HCID 67265769HCID 67265769, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

H2O (0.30 g, 7.11 mmol) was added to a solution of methyl 2-benzyl-3-oxoisoindoline-5-carboxylate (Chemical Formula 7) (0.5 g, 1.78 mmol) in a mixture of 3:1:1(v/v/v) THF:methanol:H20 which was then stirred for 1 hour. The reaction progress was monitored using TLC [Hex:EA=1:1]. When the reaction was completed, the pH of the reaction mixture was adjusted to 4 with 1N HCl, followed by extraction with ethyl acetate. The organic layer thus obtained was dried over anhydrous MgSO4, filtered and concentrated in a vacuum to afford 2-benzyl-3-oxoisoindoline-5-carboxylic acid (Chemical Formula 8) at a yield of 85%.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-e8fa0a1957784dfbbdda7b161ce81cb1
Source dataset
uspto-grants-2012_04
Patent number
US08148402B2

Reaction notes

Loading…