Aluminium lithium hydride → HCID 58972599, compound

HRID 2404876Notes

Reaction equation

HRID 2404876 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 58972599HCID 58972599, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)).

Workup

  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))

Sources & evidence

ORD record
ord-0aff8511530842e090c3ed4a9dbee5a2
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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