Sodium Hydroxide → HCID 86301334, compound

HRID 1748387Notes

Reaction equation

HRID 1748387 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-d38d1aa43a81408e9dc9884ad8a69ca1
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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