Ammonium Hydroxide → 1H-Inden-1-one, 3-amino-5-hydroxy-2-(4-hydroxyphenyl)-

HRID 1071219ノート

反応式

HRID 1071219 の反応式
B(Br)(Br)Br.[NH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15]C)[CH:13]=2)[C:8](=[O:17])[C:7]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=1.[OH-].[NH4+]>ClCCl>[NH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[C:8](=[O:17])[C:7]=1[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 389548NSC685853

生成物 1

HCID 102860111H-Inden-1-one, 3-amino-5-hydroxy-2-(4-hydroxyphenyl)-収率 56%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Boron tribromide (0.5 mL, 5.3 mmol) was added dropwise into a cold (−78° C.) mixture of 3-Amino-5-methoxy-2-(4-methoxyphenyl)-1H-inden-1-one (250 mg, 0.89 mmol), and dichloromethane (2.0 mL). The reaction mixture was allowed to come gradually to room temperature and stirred for 1 hour. The mixture was poured onto ice containing ammonium hydroxide (1 mL) and extracted with ethyl acetate. The organic extracts were washed with brine and were dried over MgSO4. Evaporation and flash chromatography (5%-10% ETOH/dichloromethane) gave (126 mg, 56% yield) of the product as a purple solid: mp 260-265° C.;

後処理

  1. customto come gradually to room temperature
  2. additionThe mixture was poured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialwere dried over MgSO4
  6. customEvaporation and flash chromatography (5%-10% ETOH/dichloromethane)

出典と根拠

ORDレコード
ord-4640fb60f3bc46a5b3b0977672af7e52
出典データセット
uspto-grants-2005_06
特許番号
US06903238B2

反応ノート

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