Hydrochloric Acid → HCID 67327185, compound

HRID 1023342Notes

Reaction equation

HRID 1023342 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:24](OC)=[O:25])[CH:20]=3)[N:15]=2)=[CH:11][CH:10]=1.Cl>C1COCC1>[CH3:7][O:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:24][OH:25])[CH:20]=3)[N:15]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 67327036HCID 67327036, compound

Product 1

HCID 67327185HCID 67327185, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF (39 mL) suspension of LiAlH4 (0.15 g) was slowly added methyl 2-(4-methoxyphenoxy)quinoline-6-carboxylate (1.22 g) at 0° C., then the resultant mixture was stirred over night at room temperature. The reaction mixture was acidified with 6 M aqueous HCl, and extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford [2-(4-methoxyphenoxy)quinolin-6-yl]methanol (1.11 g) as a pale yellow amorphous powder.

Workup

  1. customat 0° C.
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with water and saturated aqueous NaCl
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5de9e95895934d378bcd260c9265fc15
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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