Sodium Hydroxide → HCID 86718156, compound

HRID 2205173Notes

Reaction equation

HRID 2205173 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:27]([O:29]CC)=[O:28])[CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:27]([OH:29])=[O:28])[CH:15]=3)[N:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86718155HCID 86718155, compound

Product 1

HCID 86718156HCID 86718156, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl 2,3-bis(4-methoxyphenyl)quinoline-6-carboxylate (83 mg, 0.20 mmol, 1.00 equiv) and sodium hydroxide (40 mg, 1.00 mmol, 5.00 equiv) in methanol (10 mL) and water (1 mL) were placed in a 25-mL round-bottom flask and stirred for 3 h at 50° C. in an oil bath. The resulting mixture was concentrated under vacuum, diluted with 10 mL of H2O, and the pH adjusted to 4-5 with 1N HCl. The resulting solids were collected by filtration and dried in an oven under reduced pressure. The crude product (80 mg) was purified by Flash-Prep-HPLC (CH3CN/H2O; Detector, UV 254 nm), affording 60 mg (78%) of 2,3-bis(4-methoxyphenyl)quinoline-6-carboxylic acid as a yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additiondiluted with 10 mL of H2O
  3. filtrationThe resulting solids were collected by filtration
  4. customdried in an oven under reduced pressure
  5. customThe crude product (80 mg) was purified by Flash-Prep-HPLC (CH3CN/H2O; Detector, UV 254 nm)

Sources & evidence

ORD record
ord-09f5ea1c72a9452cb3f5a2a00adf448d
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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