4-Fluorophenylhydrazine hydrochloride → ethyl 5-acetyl-1-(4-fluorophenyl)-8-nitro-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-3-carboxylate

HRID 1348927노트

반응식

HRID 1348927 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=2)[C:7](=O)[CH:6]([C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:5]1)(=[O:3])[CH3:2].Cl.[F:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][NH2:34])=[CH:29][CH:28]=1>C(O)(=O)C>[C:1]([N:4]1[C:13]2[CH:12]=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=2[C:7]2[N:33]([C:30]3[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=3)[N:34]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 58859529Ethyl (1-acetyl-6-nitro-4-oxo-1,2,3,4-tetrahydroquinolin-3-yl)(oxo)acetate

생성물 1

HCID 21092644ethyl 5-acetyl-1-(4-fluorophenyl)-8-nitro-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-3-carboxylate수율 59%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

The material of step 3 of Example 17 (15 g, 0.044 mol) was dissolved in 100 mL of glacial acetic acid and then 4-fluorophenyl hydrazine hydrochloride (7.15 g, 0.044 mol) was added. The reaction was then stirred at room temperature for 18 hours, under argon, and then concentrated to remove most of the acetic acid. The remaining viscous oil was triturated with 250 mL acetonitrile. The resulting solid was isolated by vacuum filtration and dried to yield the product as an orange/pink solid. 11 g (MW=424.38, 59% yield). LC/MS m/z=425.2 (m+1).

후처리

  1. concentrationconcentrated
  2. customto remove most of the acetic acid
  3. customThe remaining viscous oil was triturated with 250 mL acetonitrile
  4. customThe resulting solid was isolated by vacuum filtration
  5. customdried

출처 및 근거

ORD 기록
ord-c0887708c4e246f7a65a853ac2f266b7
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211597B2

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