Sodium Hydroxide → HCID 86301334, compound

HRID 513937Notes

Reaction equation

HRID 513937 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:18]([O-:20])=O)[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Na+].F[C:25]1C=CC(COC2C=C3C(C=C(C(OCC)=O)C=N3)=CC=2)=CC=1.[OH-].[Na+]>CO.C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:18](=[O:20])[CH3:25])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 86296056HCID 86296056, compoundHCID 90416892Sodium 7-((4-fluorobenzyl)oxy)quinoline-3-carboxylate

Product 1

HCID 86301334HCID 86301334, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium 7-((4-fluorobenzyl)oxy)quinoline-3-carboxylate. To a solution of ethyl 7-[(4-fluorophenyl)methoxy]quinoline-3-carboxylate (Example 2, 430 mg, 1.32 mmol) in MeOH (2 mL) and THF (2 mL) was added NaOH (95 mg, 2.38 mmol) in H2O (2.0 mL). The reaction was stirred for 15 minutes at ambient temperature. The crude reaction mixture was concentrated under reduced pressure to afford the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.29 (d, J=2.0 Hz, 1H), 8.60 (d, J=2.0 Hz, 1H), 7.96 (d, J=9.0 Hz, 1H), 7.63 (dd, J=5.5, 8.6 Hz, 2H), 7.50 (d, J=2.7 Hz, 1H), 7.35-7.25 (m, 3H), 5.31 (s, 2H). [M+H]=298.2

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-73f679e9ac864e88a33d2b184e25415f
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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