Sodium Hydroxide → HCID 13756054, compound

HRID 1904703Notes

Reaction equation

HRID 1904703 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[C:5]([N+:17]([O-])=O)[CH:4]=2.[OH-].[Na+]>C(O)(=O)C.[Pd]>[NH2:17][C:5]1[CH:4]=[C:3]2[C:8]([N:9]=[C:10]3[C:15](=[C:2]2[NH2:1])[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 620863HCID 620863, compound

Product 1

HCID 13756054HCID 13756054, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

In 250 ml of glacial acetic acid was dissolved 4.43 g of 9-amino-3,4-dihydro-7-nitroacridin-1(2H)-one and 0.44 g of 10% Pd/C was added. The mixture was put in a 500 ml hydrogenation vessel (Parr) and was shaken under 55 psig (initial) H2. The uptake of H2 was 3 eq before the reaction as complete. The reaction was poured into ice and made basic with 10% NaOH. The precipitate was filtered and dissolved in MeOH. The insoluble Pd/C catalyst was filtered off and the filtrate was diluted with toluene and concentrated until crystallization occurred. The yield was 2.84 g (73%) of a solid, melting point 310° C.

Workup

  1. additionwas added
  2. customThe mixture was put in a 500 ml hydrogenation vessel
  3. custombefore the reaction as complete
  4. additionThe reaction was poured into ice
  5. filtrationThe precipitate was filtered
  6. dissolutiondissolved in MeOH
  7. filtrationThe insoluble Pd/C catalyst was filtered off
  8. additionthe filtrate was diluted with toluene
  9. concentrationconcentrated until crystallization

Sources & evidence

ORD record
ord-7dc2a5a4020d49dc889091caea6fa654
Source dataset
uspto-grants-1989_06
Patent number
US04839364

Reaction notes

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