Acetic Anhydride → 2-Acetoxy-8-hydroxyquinoline

HRID 263962Notes

Reaction equation

HRID 263962 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N+:10]([O-])=[CH:9][CH:8]=[CH:7]2.[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>>[C:13]([O:16][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([OH:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1)(=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 143128-Hydroxyquinoline N-oxide

Product 1

HCID 229959082-Acetoxy-8-hydroxyquinolineYield 84%

Procedure

A mixture of 5a (0.81 g, 5 mmol) in acetic anhydride (20 ml) was heated at reflux for 2 h (monitored by TLC). After cooling, it was poured into ice water (100 ml). The resulting solid was collected and crystallized from dichloromethane to give 2-Acetoxy-8-hydroxyquinoline (5b) (0.85 g, 84%) as white crystals. mp: 240°-241° C.; 1H-NMR (DMSO-d6): δ2.55; (s, 3H, CH3), 6.66 (d, 3-H), 7.15-7.23 (m, 3H, Ar--H), 7.78 (d, 4-H), 11.31 (br s, 1H, OH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h (monitored by TLC)
  3. temperatureAfter cooling
  4. customThe resulting solid was collected
  5. customcrystallized from dichloromethane

Sources & evidence

ORD record
ord-bc6e806dbf364725806bdc33ed6a059a
Source dataset
uspto-grants-1997_07
Patent number
US05646164

Reaction notes

Loading…