Sodium Hydroxide → HCID 56959485, compound

HRID 55827Notes

Reaction equation

HRID 55827 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:22])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)[CH:8]=[CH:7]2.C(OC1C=C2C(=C(F)C=1)N=C(C1C=CC(C(OC)=O)=CC=1)C=C2)(=O)C.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([OH:22])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66980066Methyl 4-(6-acetoxy-8-fluoroquinolin-2-yl)benzoateHCID 66980126Methyl 4-(8-fluoro-6-hydroxyquinolin-2-yl)benzoate

Product 1

HCID 56959485HCID 56959485, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-(8-fluoro-6-hydroxyquinolin-2-yl)benzoate and methyl 4-(6-acetoxy-8-fluoroquinolin-2-yl)benzoate (120 mg) was hydrolyzed with 2N NaOH (4 mL) in MeOH (4 mL). The desired product-4-(8-fluoro-6-hydroxyquinolin-2-yl)benzoic acid (65 mg) was collected by filtration after acidification with 12N HCl. 1H NMR (DMSO-d6 300 MHz TMS): δ 8.36-8.33 (3H, m), 8.18 (1H, d, J=9 Hz), 8.09 (2H, d, J=9 Hz), 7.24 (1H, dd, J=12 and 3 Hz), 7.09 (1H, d, J=3 Hz) ppm, MS (ESI): m/z 284, [M+H+].

Workup

  1. filtrationThe desired product-4-(8-fluoro-6-hydroxyquinolin-2-yl)benzoic acid (65 mg) was collected by filtration after acidification with 12N HCl

Sources & evidence

ORD record
ord-b592438b0dc043798ff60c6a16ae46f1
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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