Water → (5-Chloro-6-quinolinyl)methanol

HRID 581995Notes

Reaction equation

HRID 581995 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:17]([C:18](OCC)=[O:19])=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.C(OC(=O)C)C.O>O1CCCC1>[Cl:7][C:8]1[C:17]([CH2:18][OH:19])=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 53760849Ethyl 5-chloroquinoline-6-carboxylate

Product 1

HCID 45588508(5-Chloro-6-quinolinyl)methanolYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithiumaluminiumhydride (1.66 g) was added portionwise to a solution of intermediate 1 (10.11 g) in tetrahydrofuran (325 ml) at 0° C. under N2 and the mixture was stirred for 1 hour. Ethylacetate (70 ml) and water (3 ml) were added to the mixture which was subsequently filtered. The filtrate was dried over MgSO4, filtered and evaporated, yielding 7.9 g (93%) 5-chloro-6-quinolinemethanol (intermediate 2).

Workup

  1. filtrationwas subsequently filtered
  2. dry with materialThe filtrate was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-7292cfb81c8f4c59bcfa6106ace7341f
Source dataset
uspto-grants-1999_07
Patent number
US05922734

Reaction notes

Loading…