Sodium Hydroxide → HCID 59402964, compound

HRID 538525Notes

Reaction equation

HRID 538525 reaction equation
F[C:2]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[OH-:18].[Na+]>S([O-])([O-])(=O)=O.[Cu+2]>[OH:18][C:2]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59402698HCID 59402698, compound

Product 1

HCID 59402964HCID 59402964, compound

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 2-fluoro-3-Hexoxy-benzamide (0.30 g, 1.2 mmol), copper sulfate (0.10 g, 0.4 mol) copper (0.015 g, 0.2 mmol) and NaOH (2.5 ml) was stirred at 100° C. for 14 hrs. After completion of reaction the reaction mixture was acidified and extracted with EtOAc. The obtained crude compound was purified by column chromatography on silica (230-4000 using ethyl acetate/hexane (50:50) as the eluent to provide the title compound as yellow (0.15 g, 50%). 1H NMR (DMSO-d6, 400 MHz with D2O): δ 3.9 (s, 3H), 7.11-7.18 (m, 2H), 7.53-7.58 (m, 1H). MS ES+ (229.0 M+2H adduct). HPLC (Method 7) Rt=11.16 min.

Workup

  1. customAfter completion of reaction the reaction mixture
  2. extractionextracted with EtOAc
  3. customThe obtained crude compound
  4. customwas purified by column chromatography on silica (230-4000 using ethyl acetate/hexane (50:50) as the eluent

Sources & evidence

ORD record
ord-2c658d621fdf4322ba39b67b6940f023
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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