Aluminium lithium hydride → HCID 86301489, compound

HRID 1748405Notes

Reaction equation

HRID 1748405 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:17][C:18](OCC)=[O:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:17][CH2:18][OH:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86296662HCID 86296662, compound

Product 1

HCID 86301489HCID 86301489, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled, −78° C., solution of ethyl 2-(7-((3-chlorobenzyl)oxy)quinolin-3-yl)acetate (Example 51, 50 mg, 0.14 mmol) in THF (1.5 mL), under an atmosphere of nitrogen, was added LiAlH4 (2.4 M in THF, 0.1 mL, 0.24 mmol). The reaction was stirred for 7 h before being quenched with 1N NaOH (aq.). The crude reaction mixture was filtered through CELITE® and the aqueous layer was extracted with EtOAc. The combined organic fractions were concentrated onto silica and purification (FCC, SiO2, 0-5%, MeOH/DCM) afforded the title compound as a yellow solid (29 mg, 66%). 1H NMR (400 MHz, CDCl3) δ 8.71 (d, J=2.0 Hz, 1H), 7.92 (s, 1H), 7.67 (d, J=9.0 Hz, 1H), 7.50 (s, 1H), 7.42 (d, J=2.3 Hz, 1H), 7.38-7.27 (m, 4H), 5.18 (s, 2H), 4.02-3.90 (m, 2H), 3.02 (t, J=6.3 Hz, 2H). [M+H]=314.3.

Workup

  1. custombefore being quenched with 1N NaOH (aq.)
  2. customThe crude reaction mixture
  3. filtrationwas filtered through CELITE®
  4. extractionthe aqueous layer was extracted with EtOAc
  5. concentrationThe combined organic fractions were concentrated onto silica and purification (FCC, SiO2, 0-5%, MeOH/DCM)

Sources & evidence

ORD record
ord-d8f99087f1304a598b456da3fb4bfecc
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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