Aluminium lithium hydride → HCID 86301179, compound

HRID 1748384Notes

Reaction equation

HRID 1748384 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[C:15]([C:20](OCC)=[O:21])[CH:16]=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([CH2:20][OH:21])[CH:16]=[N:17]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86296057HCID 86296057, compound

Product 1

HCID 86301179HCID 86301179, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution, −78° C., under nitrogen, of ethyl 7-[(3-chlorophenyl)methoxy]quinoline-3-carboxylate (Example 3, 172 mg, 0.50 mmol) in THF (8.0 mL) was added LiAlH4 (2.4 M in THF, 2.0 mL, 4.8 mmol). The reaction mixture was stirred for 7 h before being quenched with a 1 N NaOH (aq.) solution. The crude reaction mixture was filtered through CELITE® and the aqueous layer was extracted with EtOAc. The organic layers were combined and concentrated onto silica. Purification (FCC, SiO2, 0-5%, MeOH/DCM) afforded the title compound as a yellow solid (115 mg, 76%). 1H NMR (400 MHz, DMSO-d6) δ 8.81 (d, J=2.3 Hz, 1H), 8.20 (d, J=1.2 Hz, 1H), 7.94 (d, J=9.0 Hz, 1H), 7.64 (s, 1H), 7.57-7.43 (m, 4H), 7.37 (dd, J=2.7, 9.0 Hz, 1H), 5.43 (t, J=5.7 Hz, 1H), 5.34 (s, 2H), 4.71 (d, J=5.5 Hz, 2H). [M+H]=300.2.

Workup

  1. custombefore being quenched with a 1 N NaOH (aq.) solution
  2. customThe crude reaction mixture
  3. filtrationwas filtered through CELITE®
  4. extractionthe aqueous layer was extracted with EtOAc
  5. concentrationconcentrated onto silica
  6. customPurification (FCC, SiO2, 0-5%, MeOH/DCM)

Sources & evidence

ORD record
ord-12eaa5778b7443fca95d15c3660a952c
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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