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Aluminium lithium hydride → HCID 58972599、化合物

HRID 2404876
ノート
印刷プレビュー

反応式

HRID 2404876 の反応式
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:20])([CH3:19])[CH2:7][CH2:8][N:9]2[C:12](OC(C)(C)C)=O)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:12][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH2:1])[CH:11]=2)[C:6]([CH3:20])([CH3:19])[CH2:7][CH2:8]1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 57354996tert-Butyl 7-amino-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carboxylate

生成物 1

HCID 58972599HCID 58972599、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 7-amino-4,4-dimethyl-2,3-dihydroquinoline-1-carboxylate (100 mg, 0.36 mmol) in THF (2.2 mL) under an inert atmosphere was added LiAlH4 (1.8 mL of 1 M, 1.8 mmol) dropwise. The reaction mixture was heated to reflux and stirred for 4 h. The reaction was cooled to room temperature and quenched with of 0.4 M NaOH solution (0.6 mL), the aqueous layer was extracted with DCM, dried over Na2SO4, filtered and concentrated to an orange oil. The residue was purified via reverse phase HPLC. LC/MS: m/z 191.5 (M+H)+ at 0.92 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customquenched with of 0.4 M NaOH solution (0.6 mL)
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to an orange oil
  8. customThe residue was purified via reverse phase HPLC
  9. waitLC/MS: m/z 191.5 (M+H)+ at 0.92 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

出典と根拠

ORDレコード
ord-0aff8511530842e090c3ed4a9dbee5a2
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08802700B2

反応ノート

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