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

HRID 490551노트

반응식

HRID 490551 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.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH:45]1[CH:50]=[CH:49][C:48]([CH2:51][NH:52][NH2:53])=[CH:47][CH:46]=1.Cl.Cl.Cl>CN(C=O)C>[CH2:51]([N:52]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:53]1)[C:48]1[CH:49]=[CH:50][CH:45]=[CH:46][CH:47]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 146540Benzylhydrazine dihydrochlorideHCID 2809972-Fluoro-5-nitrobenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

생성물 1

HCID 3849951-Benzyl-5-nitro-1,2-dihydro-3h-indazol-3-one수율 35.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-fluoro-5-nitrobenzoic acid (0.5 g) in DMF (9 mL) was added TBTU (1.04 g) followed by N-ethyldiisopropylamine (2.3 mL). After 10 minutes benzylhydrazine.2HCl (0.63 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-benzyl-5-nitro-1,2-dihydro-indazol-3-one (0.26 g) as a yellow solid. MS (ESI−):268.3 ([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-c29723ba24224e10a59bfe12c3fb473a
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528158B2

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