Hydrochloric Acid → Phthalimidine

HRID 2427499Notes

Reaction equation

HRID 2427499 reaction equation
[C:1]1(=O)[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.Cl>CC(O)=O>[C:4]1(=[O:6])[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:1][NH:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 6809Phthalimide

Product 1

HCID 10199PhthalimidineYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of phthalimide (14.7 g, 100.0 mmol) in AcOH (150 mL) was added Sn0 (29.7 g, 250.0 mmol) and concentrated HCl (70 mL). The mixture was heated to reflux for two hours. The hot mixture was filtered and concentrated. The residue was taken up in CH2Cl2 and washed four times with 1M HCl, until no more precipitate was observed when saturated NaHCO3 was added to the organic phase. The organic layer was washed once with saturated NaHCO3, dried over MgSO4, filtered and concentrated to provide the title compound as a pale yellow solid (7.00 g, 53%). 1H NMR (300 MHz, CDCl3): δ 8.08 (d of d, 1H), 7.52 (m, 3H), 4.50 (s, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for two hours
  3. filtrationThe hot mixture was filtered
  4. concentrationconcentrated
  5. washwashed four times with 1M HCl
  6. additionwas added to the organic phase
  7. washThe organic layer was washed once with saturated NaHCO3
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-558c765e6642458e8a3a180f044ea1e8
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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