Lithium Hydroxide → HCID 90417158, compound

HRID 513942Notes

Reaction equation

HRID 513942 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[C:15]([C:20]([O:22]CC)=[O:21])[CH:16]=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Li+].[OH-]>CO.C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([C:20]([OH:22])=[O:21])[CH:16]=[N:17]2)=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86296057HCID 86296057, compound

Product 1

HCID 90417158HCID 90417158, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-[(3-chlorophenyl)methoxy]quinoline-3-carboxylate (Example 3, 150 mg, 0.44 mmol) in MeOH (0.7 mL) and THF (1.7 mL) was added LiOH (13 mg, 0.54 mmol) in H2O (1.7 mL). The reaction was stirred for 14 h at ambient temperature. The crude reaction mixture was concentrated to dryness under reduced pressure. 10% HCl (aq.) (6.0 mL) was added, and the precipitate was collected and dried under high pressure to afford the title compound as a white solid (106 mg, 77%). 1H NMR (400 MHz, DMSO-d6) δ 9.25 (d, J=2.3 Hz, 1H), 8.79 (d, J=2.3 Hz, 1H), 8.25 (s, 1H), 8.03 (d, J=9.4 Hz, 1H), 7.63 (s, 1H), 7.58-7.41 (m, 4H), 5.37 (s, 2H). [M+H]=314.2.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated to dryness under reduced pressure
  3. addition10% HCl (aq.) (6.0 mL) was added
  4. customthe precipitate was collected
  5. customdried under high pressure

Sources & evidence

ORD record
ord-b688690f9a44476abe57f3e641e89857
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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