Acetic Anhydride → HCID 59527213, compound

HRID 384432Notes

Reaction equation

HRID 384432 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N+:12]([O-])=[C:11]([CH3:21])[C:10]=1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:26]C(=O)C)(=[O:25])[CH3:24]>>[C:23]([O:26][CH2:21][C:11]1[C:10]([CH3:22])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N:12]=1)(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 59527026HCID 59527026, compound

Product 1

HCID 59527213HCID 59527213, compound

Procedure

4-(Benzyloxy)-2,3,6-trimethylquinoline-1-oxide (1.18 g) was dissolved in acetic anhydride (32 mL), followed by stirring at room temperature for 2 hours. After the solvent was evaporated under reduced pressure, water (50 mL) was added to the residue, followed by extraction with ethyl acetate (100 mL). The organic layer was washed sequentially with water and saturated brine, and dried. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform) to obtain [4-(benzyloxy)-3,6-dimethylquinolin-2-yl]methyl acetate (1.25 g).

Workup

  1. customAfter the solvent was evaporated under reduced pressure, water (50 mL)
  2. additionwas added to the residue
  3. extractionfollowed by extraction with ethyl acetate (100 mL)
  4. washThe organic layer was washed sequentially with water and saturated brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-77b0436e277e4311917f40b337ca5bf9
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

Loading…