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Aluminium lithium hydride → HCID 58972599, 화합물

HRID 2404876
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HRID 2404876 반응식
[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
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참가 물질

4

반응물 2

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

생성물 1

HCID 58972599HCID 58972599, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)).

후처리

  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))

출처 및 근거

ORD 기록
ord-0aff8511530842e090c3ed4a9dbee5a2
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08802700B2

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