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

HRID 490555ノート

反応式

HRID 490555 の反応式
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]

参加物

8

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]−).

後処理

  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

出典と根拠

ORDレコード
ord-e956eafa48094ea0b08f141676cf46a9
出典データセット
uspto-grants-2009_05
特許番号
US07528158B2

反応ノート

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