Ethyl Acetate → HCID 19706721, compound

HRID 726635Notes

Reaction equation

HRID 726635 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:20])=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[CH:10]=2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[OH-].[Na+]>C1COCC1.CC(C)=O>[CH3:17][O:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:18][CH3:19])[N:8]=[C:7]([CH3:20])[C:6]([CH2:4][OH:3])=[CH:15]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 11403111HCID 11403111, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 19706721HCID 19706721, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6,7-dimethoxy-2-methylquinoline-3-carboxylic acid ethyl ester (2.83 g, 10.3 mmol) in dry THF (75 ml) was added dropwise over 20 min to a stirred, ice-cooled suspension of lithium aluminiumhydride (0.39 g, 10.3 mmol) in dry THF (50 ml). The mixture was allowed to come to room temperature over 2 h and the excess lithium aluminiumhydride was decomposed by sequential careful addition of ethyl acetate, acetone and 2M NaOH. The mixture was filtered and the white gummy material was extracted twice with acetone. The filtrate and the extracts were combined and concentrated to give 2.31 g of 6,7-dimethoxy-2-methylquinoline-3-methanol.

Workup

  1. temperaturecooled
  2. filtrationThe mixture was filtered
  3. extractionthe white gummy material was extracted twice with acetone
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-65ce02bd8f584191b8e5a1064cb450ae
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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