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

HRID 1464486Notes

Reaction equation

HRID 1464486 reaction equation
[OH-:1].Cl[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:24])[C:6]([C:20]([O:22]C)=[O:21])=[N:7][N:8]2[C:13]1[CH:18]=[CH:17][C:16](Cl)=[CH:15][CH:14]=1.[ClH:25].[CH3:26][O:27][CH:28](O)[CH3:29]>>[Cl:25][C:12]1[CH:3]=[CH:4][C:9]([N:8]2[C:13]3[C:18](=[C:17]([O:1][CH2:29][CH2:28][O:27][CH3:26])[CH:16]=[CH:15][CH:14]=3)[C:5](=[O:24])[C:6]([C:20]([OH:22])=[O:21])=[N:7]2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 961HydroxideHCID 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 potassiam hydroxide (3.9 moles, pellets, 85+%) in 3.2 l 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 l of a cold 0.8N hydrochloric acid solution (3.1 moles HCl). The resulting precipitate was isolated by filtration, washed with water (2×2 l), 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 l)
  10. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-88489726ae864a86af139271e46ae383
Source dataset
uspto-grants-1994_04
Patent number
US05304672

Reaction notes

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