Hydrochloric Acid → HCID 22046651, compound

HRID 1826147Notes

Reaction equation

HRID 1826147 reaction equation
[OH-].[K+].[N+:3]([C:6]1[C:15]([O:16][CH3:17])=[C:14]([CH3:18])[C:13]([O:19][CH3:20])=[CH:12][C:7]=1[C:8]([O:10]C)=[O:9])([O-:5])=[O:4].Cl>CO>[N+:3]([C:6]1[C:15]([O:16][CH3:17])=[C:14]([CH3:18])[C:13]([O:19][CH3:20])=[CH:12][C:7]=1[C:8]([OH:10])=[O:9])([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22046733HCID 22046733, compound

Product 1

HCID 22046651HCID 22046651, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (3.71 g, 66.31 mmol) was added to a stirred solution of 188 (4.83 g, 18.95 mmol) in anhydrous methanol (80 mL) and the reaction mixture heated at reflux for 3 h. The reaction mixture was allowed to cool and acidified to pH 2 with 1 N HCl and the solid precipitate was filtered and washed with water (50 mL) and left to air dry to afford the product as a yellow-beige solid (189) (3.69 g, 15.31 mmol, 81%); 1H NMR (270 MHz, CDCl3) δ 13.88 (br s, 1H), 7.23 (s, 1H), 3.90 (s, 3H), 3.75 (s, 3H), 2.14 (s, 3H); 1C NMR (67.8 MHz, CDCl3) δ 164.09, 158.65, 150.09, 139.38, 125.70, 122.50, 107.24, 62.78, 56.34, 9.62.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. filtrationthe solid precipitate was filtered
  5. washwashed with water (50 mL)
  6. waitleft to air
  7. customdry

Sources & evidence

ORD record
ord-648370b227a848aaa390e2c573dcff15
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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