3-Hydroxyanthranilic Acid → 2-p-Tolylbenzoxazole-4-carboxylic acid

HRID 415133

반응식

HRID 415133 반응식
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].[CH3:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=O)=[CH:15][CH:14]=1.N1C=CC=CC=1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[C:13]1([CH3:12])[CH:21]=[CH:20][C:16]([C:17]2[O:1][C:2]3[C:3](=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=[CH:9][CH:10]=3)[N:11]=2)=[CH:15][CH:14]=1

참가 물질

9

반응물 5

HCID 863-Hydroxyanthranilic AcidHCID 313Hydrochloric AcidHCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 134054-Methylbenzoyl Chloride

생성물 1

HCID 666213082-p-Tolylbenzoxazole-4-carboxylic acid수율 60%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 3-hydroxyanthranilic acid (0.153 g, 1 mmol) in toluene (10 mL) was added 4-methylbenzoylchloride (0.464 g, 3 mmol) followed by pyridine (0.275 g, 3.5 mmol) at room temperature. The resulting mixture was stirred at room temperature for 30 minutes then heated to 80C for 1 hr. After this time the reaction was cooled and poured into a mixture of ethyl acetate (50 mL) and 5% aqueous hydrochloric acid (20 mL). Subsequent separation of the layers, drying the organic over MgSO4 and filtration afforded a solution. After removal of the solvent, the residue was dissolved in xylenes (20 mL) and the solution treated with p-TsOH (0.4 g, 2.1 mmol). The reaction mixture was then heated to reflux overnight. After this time the reaction was cooled and poured into water (100 mL), the organic layer separated then washed with water (100 mL). The organic was dried over MgSO4, filtered and concentrated to a solid. Recrystallization of this solid from ethyl acetate gave a white solid product, 2-p-tolylbenzo[d]oxazole-4-carboxylic acid (0.15 g, 60% yield). MS (ESI) m/e 254 [M+H]+.

후처리

  1. temperatureAfter this time the reaction was cooled
  2. customSubsequent separation of the layers
  3. customdrying the
  4. filtrationorganic over MgSO4 and filtration
  5. customafforded a solution
  6. customAfter removal of the solvent
  7. dissolutionthe residue was dissolved in xylenes (20 mL)
  8. temperatureThe reaction mixture was then heated
  9. temperatureto reflux overnight
  10. temperatureAfter this time the reaction was cooled
  11. customthe organic layer separated
  12. washthen washed with water (100 mL)
  13. dry with materialThe organic was dried over MgSO4
  14. filtrationfiltered
  15. concentrationconcentrated to a solid
  16. customRecrystallization of this solid from ethyl acetate

출처 및 근거

ORD 기록
ord-077aa96292b24018a811234f39f85d07
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088760B2

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