Hydrochloric Acid → 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 747040ノート

反応式

HRID 747040 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=[N:12]O)[CH2:6][CH2:5]2.Cl.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH2:12])[CH2:6][CH2:5]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 734461306-bromo-3,4-dihydro-1H-naphthalen-2-one Oxime

生成物 1

HCID 100595666-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of BH3-THF complex (1 M) (35.9 mL, 35.9 mmol) was added drop-wise to a stirred solution of 6-bromo-3,4-dihydro-1H-naphthalen-2-one oxime (3.450 g, 14.37 mmol) in THF (125 mL) at 0° C. The mixture was warmed to RT and to reflux for 24 h. The reaction was cooled to RT and 1 N aqueous HCl was added carefully until the mixture was acidic and the system was stirred until no further gas was evolved. The solution was made basic by the addition of NaOH and the aqueous layer was extracted with EtOAc. The combined organics were dried over MgSO4 and concentrated in vacuo to afford the crude title compound, which was purified by flash column chromatography to yield the title compound.

後処理

  1. temperatureto reflux for 24 h
  2. temperatureThe reaction was cooled to RT
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto afford the crude title compound, which
  7. customwas purified by flash column chromatography

出典と根拠

ORDレコード
ord-779a4d809a9b4db0b221c4d0a194dd52
出典データセット
uspto-grants-2008_07
特許番号
US07393852B2

反応ノート

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