Morpholine → [8-Methyl-2-(morpholin-4-yl)quinolin-3-yl]methanol

HRID 1627507Notes

Reaction equation

HRID 1627507 reaction equation
Cl[C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>>[CH3:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[C:11]([CH2:12][OH:13])=[CH:10]2

Participants

3

Reactant 2

HCID 8083MorpholineHCID 865104(2-Chloro-8-methylquinolin-3-yl)methanol

Product 1

HCID 66776973[8-Methyl-2-(morpholin-4-yl)quinolin-3-yl]methanolYield 80%

Procedure

Following the procedure described for Intermediate 60, (2-chloro-8-methyl-quinolin-3-yl)methanol (200 mg, 0.97 mmol) and morpholine (2 mL) gave the title compound (200 mg, 80%). δH (CDCl3) 7.99 (1H, s), 7.57 (1H, d, J=8.1 Hz), 7.48 (1H, d, J=7.0 Hz), 7.35-7.26 (1H, m), 4.87 (2H, s), 3.93 (4H, t, J=4.6 Hz), 3.58 (1H, s), 3.35 (4H, t, J=4.6 Hz), 2.72 (3H, s).

Sources & evidence

ORD record
ord-975adddc0cbc4da880762e0a76e2dc89
Source dataset
uspto-grants-2014_07
Patent number
US08785628B2

Reaction notes

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