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Pyridinium chloride → 6-Nitro-quinolin-7-ol

HRID 1773578
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HRID 1773578 반응식
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14].Cl.N1C=CC=CC=1>[OH-].[Na+]>[N+:13]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[OH:2])[N:10]=[CH:9][CH:8]=[CH:7]2)([O-:15])=[O:14]
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참가 물질

4

반응물 2

HCID 10176127Pyridinium chlorideHCID 580563217-Methoxy-6-nitro-quinoline

생성물 1

HCID 1362019026-Nitro-quinolin-7-ol수율 92.3%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

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온도
150 °C

실험 절차

A mixture of 7-methoxy-6-nitro-quinoline (1.5 g, 7.35 mmol) and pyridine hydrochloride (2.6 g, 22.58 mmol) was heated at 150° C. for ca. 5 hours. The residue was dissolved in an aqueous solution of sodium hydroxide (3 M) and extracted twice with ethyl acetate. The combined organic extract were washed twice with an aqueous solution of sodium hydroxide (3 M) and then discarded. The combined aqueous layers were neutralized (pH 7) by addition of concentrated hydrochloric acid and extracted 4 times with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The yellow solid residue was purified on a silica gel plug to give 1.29 g (69% yield) of 6-nitro-quinolin-7-ol as a yellow solid.

후처리

  1. extractionextracted twice with ethyl acetate
  2. extractionThe combined organic extract
  3. washwere washed twice with an aqueous solution of sodium hydroxide (3 M)
  4. additionby addition of concentrated hydrochloric acid
  5. extractionextracted 4 times with ethyl acetate
  6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe yellow solid residue was purified on a silica gel plug

출처 및 근거

ORD 기록
ord-39a6acc710f74576a20d85f61b8728af
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09255110B2

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