Hydrochloric Acid → HCID 69277665, compound

HRID 2375896Notes

Reaction equation

HRID 2375896 reaction equation
C(=[N:14][C:15]1[CH:16]=[CH:17][C:18](=[O:27])[N:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:28]>O1CCCC1>[ClH:28].[NH2:14][C:15]1[CH:16]=[CH:17][C:18](=[O:27])[N:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58710024HCID 58710024, compound

Product 1

HCID 69277665HCID 69277665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(Benzhydrylideneamino)-1-phenyl-1H-pyridin-2-one (72.0 mg) was dissolved in tetrahydrofuran (3 ml), and aqueous HCl (2 M, 1.0 ml) was added while stirring at rt. The yellow color was faded. After 30 min, the reaction mixture was partitioned between aqueous HCl (1 M, 8 ml) and 40% EtOAc/hexane (15 ml). The aqueous layer was extracted with 40% EtOAc/hexane (15 ml), and the aqueous phase was then concentrated in vacuo to the title compound as beige foam. 1H NMR (DMSO-d6, 400 MHz): δ=6.62 (d, 1H, J=10.0 Hz), 7.42-7.59 (m, 6H), 7.90 (d, 1H, J=2.8 Hz), 10.34 (brs, 2H). MS(ES+): m/z 187.22 (100) [MH+]. HPLC: tR=0.52 min (ZQ2000, polar—5 min).

Workup

  1. customthe reaction mixture was partitioned between aqueous HCl (1 M, 8 ml) and 40% EtOAc/hexane (15 ml)
  2. extractionThe aqueous layer was extracted with 40% EtOAc/hexane (15 ml)
  3. concentrationthe aqueous phase was then concentrated in vacuo to the title compound as beige foam
  4. customHPLC: tR=0.52 min (ZQ2000, polar—5 min)

Sources & evidence

ORD record
ord-254dd63195f24a42b75faa0d9c7c2314
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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