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

HRID 490551ノート

反応式

HRID 490551 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.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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]−).

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-c29723ba24224e10a59bfe12c3fb473a
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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