Sodium Hydroxide → HCID 20512361, compound

HRID 1164401Notes

Reaction equation

HRID 1164401 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][C:14]=1[N+:22]([O-])=O)([O-])=O.[OH-].[Na+]>O.[Pd].[Pt]=O>[CH:6]1[C:5]2[C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][C:14]=3[N:22]=[N:1][C:4]=2[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 1795252,2'-Dinitro[1,1'-biphenyl]-4,4'-dicarboxylic acid

Product 1

HCID 20512361HCID 20512361, compoundYield 63.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 962WaterSolvent

Procedure

16.8 g (0.05 mol) of 2,2'-dinitro-biphenyl-4,4'-dicarboxylic acid are dissolved in 150 ml of water and 13.5 g (0.1 mol) of 30% sodium hydroxide solution. 100 mg of palladium-on-active charcoal (10%) and 50 mg of platinum oxide are added and the mixture is hydrogenated under normal pressure. 4.7 l of hydrogen are absorbed. The catalyst is filtered off with suction and the filtrate is rendered slightly acid. The precipitate is filtered off with suction and recrystallised from dimethylsulfoxide. 8.5 g (63.4%) of benzo-[c]-cinnoline-3,8-dicarboxylic acid are obtained.

Workup

  1. custom4.7 l of hydrogen are absorbed
  2. filtrationThe catalyst is filtered off with suction
  3. filtrationThe precipitate is filtered off with suction
  4. customrecrystallised from dimethylsulfoxide

Sources & evidence

ORD record
ord-cd58dde64ce14826af0e7617610bcfa7
Source dataset
uspto-grants-1983_01
Patent number
US04369318

Reaction notes

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