Sodium Hydroxide → HCID 21252883, compound

HRID 1531016Notes

Reaction equation

HRID 1531016 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[C:17]([CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:16](=O)[C:8]4[CH:9]=[C:10]([Cl:15])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.N([O-])=[O:28].[Na+].[OH-:31].[Na+]>S(=O)(=O)(O)O.O>[Cl:15][C:10]1[CH:11]=[C:12]2[C:7]3=[C:8]([C:16](=[O:31])[C:17]([CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)=[CH:18][N:6]3[C:5]3[CH:4]=[CH:3][C:2]([OH:28])=[CH:14][C:13]2=3)[CH:9]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21252836HCID 21252836, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21252883HCID 21252883, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent2×

Procedure

10-amino-2-chloro-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (300 mg) obtained in Example 273 was dissolved in a mixed solvent of conc. sulfuric acid (14.6 ml) and water (20 ml) and sodium nitrite (63 mg) dissolved in water (1 ml) was added dropwise in an ice bath. A mixed solvent of conc. sulfuric acid (20 ml) and water (15 ml) was heated under reflux in an argon atmosphere. After adding dropwise thereto the solution previously prepared, the mixture was stirred for 5 minutes and allowed to cool. The mixture was adjusted to pH 9 with 1 N aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with methanol and ether in succession to obtain the title compound (213 mg, 71%).

Workup

  1. additionwas added dropwise in an ice bath
  2. temperatureunder reflux in an argon atmosphere
  3. additionAfter adding dropwise
  4. customthe solution previously prepared
  5. temperatureto cool
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. washThe residue was washed with methanol and ether in succession

Sources & evidence

ORD record
ord-b12ffa131a0e4e01bd6097ef80af26f7
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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