Sodium borohydride → (8-Chloro-2-(2-trifluoromethylphenyl)quinolin-3-yl)methanol

HRID 2074497Notes

Reaction equation

HRID 2074497 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])[C:8]([CH:22]=[O:23])=[CH:7]2.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:19])([F:20])[F:21])[C:8]([CH2:22][OH:23])=[CH:7]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 575561672-(2-Trifluoromethylphenyl)-8-chloroquinoline-3-carbaldehyde

Product 1

HCID 57556184(8-Chloro-2-(2-trifluoromethylphenyl)quinolin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to Procedure B using 8-chloro-2-(2-trifluoromethylphenyl) quinoline-3-carbaldehyde (1.10 g, 3.28 mmol) and sodium borohydride (0.186 g, 4.91 mmol, 1.5 eq) in THF (15 mL). (8-chloro-2-(2-trifluoromethylphenyl)quinolin-3-yl)methanol was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.57 (1 H, s), 8.10 (1 H, dd, J=7.9, 1.2 Hz), 7.94 (2 H, t, J=6.4 Hz), 7.82 (1 H, t, J=7.6 Hz), 7.76 (1 H, t, J=7.6 Hz), 7.50-7.68 (4 H, m), 5.54 (1H, t, J=5.2 Hz), 4.45 (1 H, br d), 4.28 (1 H, br d) Mass Spectrum (ESI) m/e=338.0 and 340.0 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a734f02c06134622bbb3c1f683456995
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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