Hydrochloric Acid → 2-Fluoro-4-methoxyaniline

HRID 257344ノート

反応式

HRID 257344 の反応式
N([O-])=O.[Na+].[ClH:5].[Sn](Cl)Cl.NN.CCOC(C1C(=O)CCCC1)=O.[F:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[N:32]1[C:40](=O)[C:39]2[CH2:38][CH2:37][CH2:36][CH2:35][C:34]=2[NH:33]1>P(Cl)(Cl)(Cl)=O.C(O)(=O)C>[F:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[NH2:32].[Cl:5][C:40]1[N:32]([C:25]2[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:24]=2[F:23])[N:33]=[C:34]2[C:39]=1[CH2:38][CH2:37][CH2:36][CH2:35]2

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 24479Stannous ChlorideHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 189810182-(2-fluoro-4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-indazol-3-oneHCID 23668193Sodium Nitrite

生成物 2

HCID 37563832-Fluoro-4-methoxyanilineHCID 189810153-Chloro-2-(2-fluoro-4-methoxyphenyl)-4,5,6,7-tetrahydroindazole

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 24813Phosphorus oxychloride溶媒

実験手順

The diazonium salt of 2-fluoro-4-methoxyaniline was prepared using sodium nitrite and hydrochloric acid and was then reduced in situ with tin(II) chloride to prepare the correspondingly substituted phenylhydrazine (XIX). Reaction of this hydrazine with ethyl 2-cyclohexanonecarboxylate and subsequent heating of the product in the presence of acetic acid produced a mixture of 2-(2-fluoro-4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-indazol-3-one (XX) and the 2-fluoro-4-methoxyphenylhydrazone of 2-cyclohexanonecarboxylic acid. This mixture was heated in phosphorus oxychloride, yielding 3-chloro-2-(2-fluoro-4-methoxyphenyl)-4,5,6,7-tetrahydroindazole (XXI), which was then cleaved with boron tribromide to the desired 3-chloro-2-(2-fluoro-4-hydroxyphenyl)-4,5,6,7-tetrahydroindazole (XXII). ##STR13##

後処理

  1. customproduced

出典と根拠

ORDレコード
ord-a22234a6d986445c8829bacfedbf59ab
出典データセット
uspto-grants-1993_11
特許番号
US05262390

反応ノート

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