Acetic Acid → 5-Nitroquinoline-8-carboxylic acid

HRID 751061

반응식

HRID 751061 반응식
CC1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[OH-].[Na+].[CH3:17][C:18]([OH:20])=[O:19]>OS(O)(=O)=O.O>[N+:12]([C:5]1[CH:4]=[CH:3][C:17]([C:18]([OH:20])=[O:19])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)([O-:14])=[O:13]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 2463008-Methyl-5-nitroquinoline

생성물 1

HCID 154053315-Nitroquinoline-8-carboxylic acid수율 66%

시약·촉매·용매 2

HCID 962Water용매HCID 1118Sulfuric Acid용매

반응 조건

온도
0 °C

실험 절차

Compound 12A (1.0 g, 5.3 mmol) was dissolved in concentrated H2SO4 (7 mL), cooled to 0° C., and then CrO3 (2.12 g, 21.3 mmol) was added portionwise over 30 min. After the addition, the reaction mixture was warmed to rt and then heated to 80° C. for 1 h. After cooling to rt, the reaction was diluted with water, basified with 15% aqueous NaOH, then reacidified to pH=3 with AcOH, and extracted with EtOAc (4×100 mL). The combined EtOAc extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to yield the title compound (760 mg, 66%) as a yellow solid. LC/MS m/z 219 [M+H]+.

후처리

  1. additionAfter the addition
  2. temperaturethe reaction mixture was warmed to rt
  3. temperatureheated to 80° C. for 1 h
  4. temperatureAfter cooling to rt
  5. extractionextracted with EtOAc (4×100 mL)
  6. washThe combined EtOAc extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6d689d6f13294778b87a5832aae10145
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405234B2

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