2-Methyl-2-butene → HCID 19592401, compound

HRID 613534Notes

Reaction equation

HRID 613534 reaction equation
P([O-])(O)(O)=O.[Na+].CC(=CC)C.[Cl:12][C:13]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:14]=1[C:15]([NH:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]=[CH:25][C:24]([CH2:28][CH3:29])=[C:23]2[CH:30]=[O:31])=[O:16].Cl([O-])=[O:38].[Na+]>C(O)(C)(C)C.O>[C:30]([C:23]1[C:22]2[C:27](=[C:18]([NH:17][C:15](=[O:16])[C:14]3[C:32]([Cl:36])=[CH:33][CH:34]=[CH:35][C:13]=3[Cl:12])[CH:19]=[CH:20][CH:21]=2)[N:26]=[CH:25][C:24]=1[CH2:28][CH3:29])([OH:38])=[O:31]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 19592404HCID 19592404, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 19592401HCID 19592401, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of sodium dihydrogenphosphate (395 mg) and 2-methyl-2-butene (578 mg) in tert-butanol (6 ml) and water (1.5 ml) was added 8-(2,6-dichlorobenzoylamino)-3-ethyl-4-formylquinoline (615 mg) at ambient temperature, and to the mixture was portionwise added sodium chlorite (298 mg) at the same temperature. The mixture was stirred for 3 hours at the same temperature. The mixture was quenched by diluted hydrochloric acid and extracted with dichloromethane. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethyl acetate-n-hexane to give 4-carboxy-8-(2,6-dichlorobenzoylamino)-3-ethylquinoline (404 mg).

Workup

  1. customThe mixture was quenched by diluted hydrochloric acid
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-703e40e2b6a24df790f97361f0e22b43
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…