HCID 86751038, compound → HCID 86748545, compound

HRID 1608561Notes

Reaction equation

HRID 1608561 reaction equation
COC1C=CC([N:9]2[C@H:12]([CH:13]=[C:14]([CH3:16])[CH3:15])[C@H:11]([O:17][C:18](=[O:20])[CH3:19])[C:10]2=[O:21])=CC=1>C(#N)C.O>[C:18]([O:17][C@H:11]1[C@@H:12]([CH:13]=[C:14]([CH3:16])[CH3:15])[NH:9][C:10]1=[O:21])(=[O:20])[CH3:19]

Participants

4

Reactant 1

HCID 86751038HCID 86751038, compound

Product 1

HCID 86748545HCID 86748545, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of the N-aryl lactam XIV (4.88 g, 16.2 mmol) was dissolved in acetonitrile (50 mL) and cooled to 0°-5° C. in an ice bath. To this was added a cold solution of ceric ammonium nitrate (26.6 g, 48.6 mmol, 50 mL) in one portion. The deep red reaction was allowed to stir for 10 min and during that time the color gradually lightened to orange. The cold solution was transferred to a separatory funnel, diluted with water, and extracted with ethyl acetate. The organic fraction was washed with several portions of 10% aqueous sodium sulfite, followed by saturated aqueous sodium bicarbonate. The organic fraction was dried (MgSO4) and concentrated to give the desired product (2.71 g, 91%) as a yellow-orange solid that was used directly in the next step; 1H NMR (300 MHz, CDCl3): δ 6.11 (bs, 1H), 5.73 (dd, 1H, J=2.2, 4.7 Hz), 5.12-5.08 (m, 1H), 4.63 (dd, 1H, 4.7, 9.1 Hz), 2.09 (s, 3H), 1.75 (s, 3H), 1.67 (s, 3H).

Workup

  1. temperaturecooled to 0°-5° C. in an ice bath
  2. customThe deep red reaction
  3. customThe cold solution was transferred to a separatory funnel
  4. extractionextracted with ethyl acetate
  5. washThe organic fraction was washed with several portions of 10% aqueous sodium sulfite
  6. dry with materialThe organic fraction was dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ce9dc270696f4a59a7b22413fdf30e5c
Source dataset
uspto-grants-1995_03
Patent number
US05395850

Reaction notes

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