Hydrochloric Acid → 1-(4-Chlorophenyl)-5-(2-methoxyethoxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid

HRID 2081247Notes

Reaction equation

HRID 2081247 reaction equation
[OH-:1].[K+].[CH3:3][O:4][CH:5](O)[CH3:6].Cl[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:30])[C:12]([C:26]([O:28]C)=[O:27])=[N:13][N:14]2[C:19]1[CH:24]=[CH:23][C:22](Cl)=[CH:21][CH:20]=1.[ClH:31]>>[Cl:31][C:18]1[CH:9]=[CH:10][C:15]([N:14]2[C:19]3[C:24](=[C:23]([O:1][CH2:6][CH2:5][O:4][CH3:3])[CH:22]=[CH:21][CH:20]=3)[C:11](=[O:30])[C:12]([C:26]([OH:28])=[O:27])=[N:13]2)=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 30156371-MethoxyethanolHCID 10904198HCID 10904198, compound

Product 1

HCID 109157501-(4-Chlorophenyl)-5-(2-methoxyethoxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acidYield 98%

Conditions

Temperature
50 °C

Procedure

A solution of 255 g of potassium hydroxide (3.9 moles, pellets, 85+%) in 3.2 1 of methoxyethanol was stirred at 45° C. as 450 g of solid methyl phenylcinnoline-carboxylate (1.29 moles) from step 3 was added in portions. The reaction vessel was fitted with a distillation head and placed under reduced pressure (approx. 40 mmHg). The reaction was heated at 50° C. for 1 hr., then at 65° C. for 1 hr. to distill off methanol and some methoxyethanol (total volume removed 280 ml). The distillation head was replaced with a reflux condenser and the reaction was heated between 90° C. and 110° C. for 1 hr. The reaction was allowed to cool to 50° C. before the addition of 1 liter of water and was cooled to 25° C. before the resulting slurry was poured into 4 1 of a cold 0.8 N hydrochloric acid solution (3.1 moles HCl). The resulting precipitate was isolated by filtration, washed with water (2×2 1), and dried under reduced pressure at 50° C. to give 472 g (98%) of an off-white solid.

Workup

  1. additionwas added in portions
  2. customThe reaction vessel was fitted with a distillation head
  3. distillationto distill off methanol
  4. customThe distillation head was replaced with a reflux condenser
  5. temperaturethe reaction was heated between 90° C. and 110° C. for 1 hr
  6. temperatureto cool to 50° C. before the addition of 1 liter of water
  7. temperaturewas cooled to 25° C. before the resulting slurry
  8. customThe resulting precipitate was isolated by filtration
  9. washwashed with water (2×2 1)
  10. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-272a59a85a1e44b88b67d5ba51fdfcd1
Source dataset
uspto-grants-1993_02
Patent number
US05183891

Reaction notes

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