Sodium Hydroxide → HCID 178423905, compound

HRID 255861Notes

Reaction equation

HRID 255861 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][N:10]=[C:11]([C:15](Cl)=[O:16])[C:12](Cl)=[O:13])C.[OH-:18].[Na+]>ClC1C=CC=CC=1.O.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[N:9]=[N:10][C:11]([C:12]([OH:13])=[O:18])=[C:15]2[OH:16]

Participants

6

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 20164605HCID 20164605, compound

Product 1

HCID 178423905HCID 178423905, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Procedure

16.4 g of titanium tetrachloride was added to a stirred solution of 22.5 g of 53C in 160 ml of chlorobenzene, under nitrogen, at 20° C. The mixture was heated at 90°-100° C. for 5 hours and let stand over a weekend at room temperature. Then 20 ml of a solution of 26.4 g of sodium hydroxide in 330 ml of water was added, drop-by-drop, and the mixture was stirred well and stripped of solvent to form a mush. The remainder of the sodium hydroxide solution was added, and the mixture was stirred and filtered through Celite. The filtrate was acidified with 12 N hydrochloric acid and filtered. The solid was dried under reduced pressure and dissolved in 150 ml of 2 N aqueous ammonium hydroxide solution. The solution was filtered. The filtrate was acidified with 12 N hydrochloric acid and filtered. The solid was washed with water, dried under reduced pressure and dissolved in warm ethanol. The solution was filtered and the solvent was evaporated from the filtrate, to give 8-methyl-4-hydroxy-cinnoline-3-carboxylic acid (53D), as a solid, m.p.: 230° C. (with decomposition).

Workup

  1. temperatureThe mixture was heated at 90°-100° C. for 5 hours
  2. waitlet stand over a weekend at room temperature
  3. customto form a mush
  4. stirringthe mixture was stirred
  5. filtrationfiltered through Celite
  6. filtrationfiltered
  7. customThe solid was dried under reduced pressure
  8. dissolutiondissolved in 150 ml of 2 N aqueous ammonium hydroxide solution
  9. filtrationThe solution was filtered
  10. filtrationfiltered
  11. washThe solid was washed with water
  12. customdried under reduced pressure
  13. dissolutiondissolved in warm ethanol
  14. filtrationThe solution was filtered
  15. customthe solvent was evaporated from the filtrate

Sources & evidence

ORD record
ord-3b75e74eb75e4768b3c51d7c4dadac11
Source dataset
uspto-grants-1987_10
Patent number
US04699651

Reaction notes

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