2-Phenylquinoline-7-carboxylic acid hydrochloride → (2-Phenylquinolin-7-yl)methanol

HRID 244083Notes

Reaction equation

HRID 244083 reaction equation
Cl.[C:2]1([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][C:12]([C:18](O)=[O:19])=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:2]1([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][C:12]([CH2:18][OH:19])=[CH:13][CH:14]=3)[N:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159468702-Phenylquinoline-7-carboxylic acid hydrochlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 22062823(2-Phenylquinolin-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2, to a solution of 2-phenylquinoline-7-carboxylic acid hydrochloride (144 mg, 0.5 mmol) in THF (5 mL) was added LiAlH4 (95 mg, 2.5 mmol) in two portions. The mixture was stirred at rt for 15 h, quenched with water (1 mL), and filtered through a Celite pad, which was washed with EtOAc (30 mL). The combined filtrates were dried over MgSO4, filtered, concentrated, and purified by silica gel chromatography (5% MeOH in dichloromethane) to afford the desired product. 1H-NMR (CDCl3, 400 MHz) δ 4.93 (s, 2H), 7.46-7.57 (m, 4H), 7.84 (d, J=8.4 Hz, 1H), 7.88 (d, J=8.8 Hz, 1H), 8.14-8.18 (m, 3H), 8.23 (d, J=8.4 Hz, 1H). MS (ES+): m/z 236 [MH+]. HPLC: tR=2.72 min (OpenLynx, polar—5 min).

Workup

  1. customquenched with water (1 mL)
  2. filtrationfiltered through a Celite pad, which
  3. washwas washed with EtOAc (30 mL)
  4. dry with materialThe combined filtrates were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-f3194c22ba01430a93a11aaa354a6fc3
Source dataset
uspto-grants-2014_02
Patent number
US08653268B2

Reaction notes

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