Ammonia → HCID 22139754, compound

HRID 1825869Notes

Reaction equation

HRID 1825869 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N+:10]2[O-].C(OC(=O)C)(=[O:25])C.N>>[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:25])[NH:10]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 69347098HCID 69347098, compound

Product 1

HCID 22139754HCID 22139754, compoundYield 22.2%

Conditions

Temperature
75 °C

Procedure

5-(2,4-Difluoro-phenoxy)-6-methoxy-quinoline N-oxide (1.35 g, 4.5 mmol) was mixed with 5 mL of acetic anhydride and stirred at 75° C. for 22 hours. The reaction mixture was poured on ice, neutralized with aqueous ammonia, and the resultant precipitate was filtered and washed with water. The aqueous layer was extracted with dichloromethane and the organic extract was dried over MgSO4. The solvent was removed under vacuum. The dry residue, combined with the filtered precipitate, was dissolved in a minimum amount of CH2Cl2 and purified using a Biotage system, eluting with 10–30% EtOAc/hexane to give 0.3 g (22.2%) of 5-(2,4-difluoro-phenoxy)-6-methoxy-1H-quinolin-2-one.

Workup

  1. additionThe reaction mixture was poured on ice
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with water
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. extractionthe organic extract
  6. dry with materialwas dried over MgSO4
  7. customThe solvent was removed under vacuum
  8. dissolutionwas dissolved in a minimum amount of CH2Cl2
  9. custompurified
  10. washeluting with 10–30% EtOAc/hexane

Sources & evidence

ORD record
ord-5c0d953df7204b5f962a72f5bea0d979
Source dataset
uspto-grants-2006_05
Patent number
US07049325B2

Reaction notes

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