Diisobutylaluminumhydride → HCID 11264243, compound

HRID 1374744Notes

Reaction equation

HRID 1374744 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[CH:25]=[C:24]2[C:19]([C:20]([Cl:27])=[CH:21][C:22]([CH3:26])=[N:23]2)=[CH:18][CH:17]=1)=O)C>O1CCCC1>[Cl:27][C:20]1[C:19]2[C:24](=[CH:25][C:16]([CH2:14][OH:13])=[CH:17][CH:18]=2)[N:23]=[C:22]([CH3:26])[CH:21]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 24278901HCID 24278901, compound

Product 1

HCID 11264243HCID 11264243, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutylaluminum hydride (1 M solution in tetrahydrofuran, 80 mL, 80 mmol) was added dropwise at 0° C. to a solution of 4-chloro-2-methyl-quinoline-7-carboxylic acid ethyl ester (4.42 g, 17.7 mmol) in tetrahydrofuran (90 mL), then after stirring 1 h at 0° C. the reaction was quenched by careful addition of methanol (4.5 mL) and 1 M aq. potassium sodium tartrate solution (135 mL). The two-phase mixture was stirred 30 min, then extracted twice with ethyl acetate. The organic phases were washed with brine, dried (MgSO4) and evaporated. Chromatography (SiO2, hexane/ethyl acetate 1:1 afforded the title compound (2.62 g, 71%). Off-white solid, EI-MS: m/e==207.2 (M+).

Workup

  1. customwas quenched by careful addition of methanol (4.5 mL) and 1 M aq. potassium sodium tartrate solution (135 mL)
  2. stirringThe two-phase mixture was stirred 30 min
  3. extractionextracted twice with ethyl acetate
  4. washThe organic phases were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-b8b065186bb44f589a7506f6346d24a5
Source dataset
uspto-grants-2007_01
Patent number
US07166589B2

Reaction notes

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