Water → HCID 86732737, compound

HRID 525870Notes

Reaction equation

HRID 525870 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:11]=2)[C:6](=[O:33])[C:5]([C:34]([O:36]C)=[O:35])=[N:4]1)[CH3:2].O.[K]>CO>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:10]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH:11]=2)[C:6](=[O:33])[C:5]([C:34]([OH:36])=[O:35])=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5462222PotassiumHCID 86732736HCID 86732736, compound

Product 1

HCID 86732737HCID 86732737, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of methyl 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylate (3 g, 5.95 mmol) in a mixed solvent of water (25.00 mL) and methanol (75 mL) was added potassium hydtoxide (1.668 g, 29.7 mmol). The mixture was stirred at room temperature for 0.5 h and then heated to reflux for 1 h when the yellow suspension turned into a clear yellow solution. LCMS indicated completion of the reaction. The mixture was cooled to room temperature and concentrated. The residue was dissolved in water (100 mL), and was then acidified to ˜pH 1 using aq. 6N hydrochloric acid. The white precipitates were collected by filtration, and the filtrate was extracted with ethyl acetate (2×100 mL). The combined organic layers were concentrated to provide more white solids that were combined with previous white precipitates and dried under high vacuum to afford 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid (2.8 g, 5.71 mmol, 96% yield). LCMS: (M+H)+: 491.4.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h when the yellow suspension
  3. customcompletion of the reaction
  4. temperatureThe mixture was cooled to room temperature
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in water (100 mL)
  7. customThe white precipitates
  8. filtrationwere collected by filtration
  9. extractionthe filtrate was extracted with ethyl acetate (2×100 mL)
  10. concentrationThe combined organic layers were concentrated
  11. customto provide more white solids that
  12. customwhite precipitates
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-2798341fddad40b1894628711a809352
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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