Sodium borohydride → (2-(2-Methoxyphenyl)-8-methylquinolin-3-yl)methanol

HRID 1397667Notes

Reaction equation

HRID 1397667 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]2[C:11](=[C:12]([CH3:21])[CH:13]=[CH:14][CH:15]=2)[N:10]=1.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:18]([CH2:19][OH:20])=[CH:17][C:16]2[C:11](=[C:12]([CH3:21])[CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 577079582-(2-Methoxyphenyl)-8-methylquinoline-3-carbaldehyde

Product 1

HCID 57707787(2-(2-Methoxyphenyl)-8-methylquinolin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to Procedure B using 2-(2-methoxyphenyl)-8-methylquinoline-3-carbaldehyde (0.250 g, 0.9 mmol), and sodium borohydride (0.0378 g, 1.35 mmol, 1.5 eq), in THF (5 mL). (2-(2-Methoxyphenyl)-8-methylquinolin-3-yl)-methanol was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.41 (1 H, s), 7.92 (1 H, d, J=7.8 Hz), 7.64 (1 H, d, J=7.0 Hz), 7.50-7.59 (2 H, m), 7.33 (1 H, dd, J=7.4, 1.6 Hz), 7.22 (1 H, d, J=7.8 Hz), 7.16 (1 H, t, J=7.2 Hz), 5.37 (1 H, t, J=5.5 Hz), 3.79 (3 H, s), 2.72 (3 H, s) Mass Spectrum (ESI) m/e=280.1 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-165530d273054202982782acbc44ca0d
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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