Sodium Hydroxide → HCID 21252836, compound

HRID 850809Notes

Reaction equation

HRID 850809 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12]3=[C:13]([C:15](=[O:25])[C:16]([CH2:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)=[CH:17][N:11]3[C:10]3[CH:9]=[CH:8][C:7]([N+:26]([O-])=O)=[CH:6][C:5]2=3)[CH:14]=1.[OH-].[Na+]>S(=O)(=O)(O)O.[Cu]>[NH2:26][C:7]1[CH:8]=[CH:9][C:10]2[N:11]3[CH:17]=[C:16]([CH2:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[C:15](=[O:25])[C:13]4[CH:14]=[C:2]([Cl:1])[CH:3]=[C:4]([C:5]=2[CH:6]=1)[C:12]3=4

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21252843HCID 21252843, compound

Product 1

HCID 21252836HCID 21252836, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

2-chloro-10-nitro-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (1.86 g) obtained in Example 272 was dissolved in conc. sulfuric acid (11 ml) and copper (995 mg) was added to the solution. The mixture was heated to 50° C. in a hot water bath and stirred for 30 minutes. After allowing to cool, the reaction mixture was poured into ice water, then the solution was adjusted to pH 10 with 1 N aqueous solution of sodium hydroxide. The precipitated crystals were recovered by filtration, and washed with water and ether in succession to obtain the title compound (1.37 g, 80%).

Workup

  1. temperatureto cool
  2. filtrationThe precipitated crystals were recovered by filtration
  3. washwashed with water and ether in succession

Sources & evidence

ORD record
ord-08f7bc2615a54cea9433cfcad36eb8d6
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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