Sulfuric Acid → HCID 20253651, compound

HRID 638215Notes

Reaction equation

HRID 638215 reaction equation
O.Cl.Cl.N[C:5]1[CH:6]=[C:7]([C:11]2[N:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15](=[O:21])[NH:16]3)[CH:8]=[CH:9][CH:10]=1.S(=O)(=O)(O)[OH:23].N([O-])=O.[Na+].[OH-].[NH4+]>O>[OH:23][C:5]1[CH:6]=[C:7]([C:11]2[N:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15](=[O:21])[NH:16]3)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 20253638HCID 20253638, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20253651HCID 20253651, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture containing 6.9 g of 5-(3-aminophenyl)-1,6-naphthyridin-2(1H)-one dihydrochloride monohydrate and 50 ml of water in an ice bath was slowly added 50 ml of concentrated sulfuric acid followed by 1.45 g of sodium nitrite. The reaction mixture was stirred in an ice bath for about 2 hours and then allowed to warm up to room temperature. It was next heated on a steam bath for about 2 hours and then allowed to stand at room temperature overnight. The reaction mixture was treated with ammonium hydroxide solution until it became weakly basic. The separated solid was collected, washed with water and dried in a vacuum oven at 90° C. The solid was recrystallized from boiling isopropyl alcohol using decolorizing charcoal, the mixture filtered and the filtrate concentrated until the solid separated. The solid was collected and washed with isopropyl alcohol. Additional solid was obtained by concentrating the filtrate. The solids were combined and recrystallized from dimethylformamide using decolorizing charcoal and dried in a vacuum oven at 90° C. to yield 1.3 g of 5-(3-hydroxyphenyl)-1,6-naphthyridin-2(1H)-one, m.p. 297°-299° C. with decomposition.

Workup

  1. temperatureIt was next heated on a steam bath for about 2 hours
  2. waitto stand at room temperature overnight
  3. customThe separated solid was collected
  4. washwashed with water
  5. customdried in a vacuum oven at 90° C
  6. customThe solid was recrystallized
  7. filtrationthe mixture filtered
  8. concentrationthe filtrate concentrated until the solid
  9. customseparated
  10. customThe solid was collected
  11. washwashed with isopropyl alcohol
  12. customAdditional solid was obtained
  13. concentrationby concentrating the filtrate
  14. customrecrystallized from dimethylformamide using
  15. customdried in a vacuum oven at 90° C.

Sources & evidence

ORD record
ord-9629ac2485214f7caa6310ed5419c9d9
Source dataset
uspto-grants-1985_12
Patent number
US04560691

Reaction notes

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