Diisobutylaluminum hydride → [8-Chloro-2-(pyridin-3-yl)quinolin-3-yl]methanol

HRID 572122Notes

Reaction equation

HRID 572122 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])=O)C.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Cl:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C:6]([CH2:4][OH:3])=[CH:15]2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 666920418-Chloro-2-(pyridin-3-yl)quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 66691162[8-Chloro-2-(pyridin-3-yl)quinolin-3-yl]methanolYield 99.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 8-chloro-2-(pyridin-3-yl)quinoline-3-carboxylic acid ethyl ester (1.0 g, 3.2 mmol) in toluene at −78° C. was added a solution of DIBAL-H (10 mL, 1M in DCM) dropwise over 10 minutes. The mixture was stirred at this temperature for 2 h, then quenched by the addition of a saturated aqueous solution of Rochelle salt (5 mL). After warming to room temperature, extra Rochelle salt solution (5 mL) was added. The resulting solid was filtered, washed on the sinter with aqueous NaOH solution (2N) and water, and dried to give [8-chloro-2-(pyridin-3-yl)quinolin-3-yl]methanol (860 mg, quantitative) as a beige solid. δH (DMSO-d6) 8.92 (d, J 1.7 Hz, 1H), 8.73 (dd, J 4.8, 1.6 Hz, 1H), 8.61 (s, 1H), 8.17 (dt, J 7.9, 1.9 Hz, 1H), 8.09 (dd, J 8.2, 1.1 Hz, 1H), 7.97 (dd, J 7.5, 1.2 Hz, 1H), 7.63 (m, 1H), 7.58 (ddd, J 7.8, 4.8, 0.6 Hz, 1H), 5.76 (s, 1H), 5.62 (t, J 5.2 Hz, 1H), 4.68 (d, J 4.9 Hz, 2H). LCMS (ES+) 271.0 (M+H)+.

Workup

  1. customquenched by the addition of a saturated aqueous solution of Rochelle salt (5 mL)
  2. additionextra Rochelle salt solution (5 mL) was added
  3. filtrationThe resulting solid was filtered
  4. washwashed on the sinter with aqueous NaOH solution (2N) and water
  5. customdried

Sources & evidence

ORD record
ord-6193b822b7314dfc9fe9a5c08dd95dd2
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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