Sodium borohydride → (2-(2-Chlorophenyl)-8-chloroquinolin-3-yl)methanol

HRID 216746Notes

Reaction equation

HRID 216746 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH:18]=[O:19])=[CH:16][C:15]2[C:10](=[C:11]([Cl:20])[CH:12]=[CH:13][CH:14]=2)[N:9]=1.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH2:18][OH:19])=[CH:16][C:15]2[C:10](=[C:11]([Cl:20])[CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 577078842-(2-Chlorophenyl)-8-chloroquinoline-3-carbaldehyde

Product 1

HCID 57707777(2-(2-Chlorophenyl)-8-chloroquinolin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to Procedure B using 2-(2-chlorophenyl)-8-chloroquinoline-3-carbaldehyde (1.18 g, 3.9 mmol), and sodium borohydride (0.222 g, 5.86 mmol, 1.5 eq) in THF (20 mL). (2-(2-chlorophenyl)-8-chloroquinolin-3-yl)methanol was obtained as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.56 (1H, s), 8.10 (1H, dd, J=8.2, 1.2 Hz), 7.94 (1H, dd, J=7.6, 1.4 Hz), 7.63 (2H, t, J=7.8 Hz), 7.44-7.59 (3H, m), 5.54 (1H, t, J=5.3 Hz) Mass Spectrum (ESI) m/e=304.0 and 306.1 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-d4d7c31f1ebd45ae99c1618b53e1098c
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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