Quinoline-5-carboxylic acid → (Quinolin-5-yl)methanol

HRID 1819450Notes

Reaction equation

HRID 1819450 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11](O)=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:1]1[C:10]2[C:5](=[C:6]([CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 232489Quinoline-5-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 823080(Quinolin-5-yl)methanolYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of quinoline-5-carboxylic acid (500 mg, 2.83 mmol) in THF (10 mL) was added slowly LiAlH4 (1.0 M, THF) solution at 0° C. The resulting residue was heated to 70° C. for 3 h and stirred at room temperature for 16 h. The reaction mixture was cooled to 0° C. and quenched with water (1 mL) and 10% NaOH (1.5 mL) solution. The reaction mixture was stirred for 1 h. The solution was filtered through a pad of celite and rinsed with THF. The filtrate was concentrated and the resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 218 mg of quinolin-5-yl-methanol (48%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with water (1 mL) and 10% NaOH (1.5 mL) solution
  3. stirringThe reaction mixture was stirred for 1 h
  4. filtrationThe solution was filtered through a pad of celite
  5. washrinsed with THF
  6. concentrationThe filtrate was concentrated
  7. customthe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-1b0073189daf4396a6c27c2bbffe4b62
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

Loading…