Hydrochloric Acid → 1-Isobutyl-5-nitro-1,2-dihydro-indazol-3-one

HRID 490555노트

반응식

HRID 490555 반응식
F[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.CCN=C=NCCCN(C)C.Cl.C(N(C(C)C)C(C)C)C.[CH2:35]([NH:39][NH2:40])[CH:36]([CH3:38])[CH3:37].C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>CN(C=O)C>[CH2:35]([N:39]1[C:2]2[C:3](=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)[C:4](=[O:6])[NH:40]1)[CH:36]([CH3:38])[CH3:37]

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 81531DiisopropylethylamineHCID 2809972-Fluoro-5-nitrobenzoic acidHCID 542420IsobutylhydrazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 688321981-Isobutyl-5-nitro-1,2-dihydro-indazol-3-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-fluoro-5-nitrobenzoic acid (1.5 g) in DMF (50 mL) was added EDCI.HCl (1.71 g) followed by N-ethyldiisopropylamine (5.51 mL). After 10 minutes isobutylhydrazine.p-toluenesulfonicacid salt (2.32 g) was added. The reaction mixture was stirred at ambient temperature for 22 hours and the reaction was poured onto aqueous 1N HCl solution and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo. Purification via ISCO combiflash chromatography afforded pure desired 1-isobutyl-5-nitro-1,2-dihydro-indazol-3-one (0.9 g) as a yellow solid. MS (ESI−):234.1 ([M−H]−).

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification via ISCO combiflash chromatography

출처 및 근거

ORD 기록
ord-e956eafa48094ea0b08f141676cf46a9
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528158B2

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