Acrolein → 7-Methoxyquinoline-8-carboxylic acid

HRID 2175942Notes

Reaction equation

HRID 2175942 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].[CH:13]([CH:15]=[CH2:16])=O>O1CCOCC1>[CH3:12][O:11][C:7]1[C:3]([C:4]([OH:6])=[O:5])=[C:2]2[C:10]([CH:13]=[CH:15][CH:16]=[N:1]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7847AcroleinHCID 27353572-Amino-6-methoxybenzoic Acid

Product 1

HCID 687745837-Methoxyquinoline-8-carboxylic acidYield 20.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
200 °C

Procedure

In 1 g separate batches a mixture of 2-amino-6-methoxybenzoic acid (11 g, 66 mmol) and acrolein (4.8 mL, 72 mmol) in 1,4-dioxane (66 mL) was heated in a microwave reactor for 20 min at 200° C. After combining the reactions, the mixture was concentrated and purified via silica gel chromatography (0-10% MeOH in DCM) to give the title compound (2.8 g, 20%). MS (ESI) mass calcd. for C11H19NO3, 203.1; m/z found 204.0 [M+H]+.

Workup

  1. customIn 1 g separate batches
  2. concentrationthe mixture was concentrated
  3. custompurified via silica gel chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-9f8cf45e0cd546d3a1542e493bf9aa30
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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