Methane → 9-Iodo-3-methyl-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxylic acid

HRID 1168530노트

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HRID 1168530 반응식
F[C:2]1[C:21](F)=[CH:20][C:19]([I:23])=[CH:18][C:3]=1[C:4]([C:6](=[CH:12][NH:13][N:14]([CH:16]=[O:17])[CH3:15])[C:7]([O:9]CC)=[O:8])=[O:5].[OH-].[K+].C>O>[I:23][C:19]1[CH:18]=[C:3]2[C:2]3=[C:21]([O:17][CH2:16][N:14]([CH3:15])[N:13]3[CH:12]=[C:6]([C:7]([OH:9])=[O:8])[C:4]2=[O:5])[CH:20]=1

참가 물질

5

반응물 3

HCID 297MethaneHCID 14797Potassium HydroxideHCID 178472137HCID 178472137, 화합물

생성물 1

HCID 120830559-Iodo-3-methyl-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxylic acid수율 29.1%

시약·촉매·용매 1

HCID 962Water용매

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온도
105 °C

실험 절차

Ethyl 2-(2,3-difluoro-5-iodobenzoyl)-3-(2-formyl-2-methylhydrazino)prop-2-enoate (Preparation 30, 1.02 g) in 8 mL of water is treated with KOH pellets (0.410 g) and the reaction mixture is heated in an oil bath, under a nitrogen atmosphere, at 105° C. for 1.75 h while volatiles were condensed into a Dean-Stark trap. At this time, the Dean-Stark trap was removed, 1 mL of an aqueous solution of KOH (0.956 g) is added to the mixture, and heating is continued at 105° C. for 4 days. The mixture is cooled to room temperature, treated with formic acid (1.68 g), and is warmed to 45-50° C. A 37% aqueous formaldehyde (0.396 g) is added and the mixture is heated at 70° C. for 30 minutes. The resulting slurry is cooled in an ice bath at 0-5° C., reacted with 29% aqueous ammonium hydroxide (1.46 mL), and allowed to warm to room temperature where it is stirred for 35-40 minutes. Charcoal (44 mg) is added to the mixture which is stirred for 30 minutes and filtered through a pad of solka-floc rinsing with water. The filtrate is diluted with saturated brine and a mixture of chloroform/methanol (95/5) and filtered through a pad of solka-floc. The organic layer is separated, dried with anhydrous sodium sulfate, and concentrated at reduced pressure to obtain 252 mg (28%) of the title compound. Physical characteristics: MS (ESI+) m/z 373 (M+H)+.

후처리

  1. customcondensed into a Dean-Stark trap
  2. customAt this time, the Dean-Stark trap was removed
  3. addition1 mL of an aqueous solution of KOH (0.956 g) is added to the mixture
  4. temperatureheating
  5. temperatureThe mixture is cooled to room temperature
  6. additiontreated with formic acid (1.68 g)
  7. temperatureis warmed to 45-50° C
  8. additionA 37% aqueous formaldehyde (0.396 g) is added
  9. temperaturethe mixture is heated at 70° C. for 30 minutes
  10. temperatureThe resulting slurry is cooled in an ice bath at 0-5° C.
  11. customreacted with 29% aqueous ammonium hydroxide (1.46 mL)
  12. temperatureto warm to room temperature where it
  13. stirringis stirred for 30 minutes
  14. filtrationfiltered through a pad of solka-floc rinsing with water
  15. additionThe filtrate is diluted with saturated brine
  16. additiona mixture of chloroform/methanol (95/5)
  17. filtrationfiltered through a pad of solka-floc
  18. customThe organic layer is separated
  19. dry with materialdried with anhydrous sodium sulfate
  20. concentrationconcentrated at reduced pressure

출처 및 근거

ORD 기록
ord-9c197df9f49b4370a540589ee9ba6eb9
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06624159B2

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