HCID 1185820, compound → HCID 22117868, compound

HRID 1740445Notes

Reaction equation

HRID 1740445 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:15][C:14]2[NH:13][C:12]3[CH2:11][C:10]([CH3:17])([CH3:16])[CH2:9][C:8](=[O:18])[C:7]=3[CH:6]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=3)[C:5]=2[C:4](=[O:28])[CH2:3]1.[H][H]>C(O)C.Cl.[Pd]>[CH3:16][C:10]1([CH3:17])[CH2:11][C:12]2[NH:13][C:14]3[CH2:15][C:2]([CH3:1])([CH3:29])[CH2:3][C:4](=[O:28])[C:5]=3[CH:6]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=3)[C:7]=2[C:8](=[O:18])[CH2:9]1

Participants

6

Reactant 2

HCID 1185820HCID 1185820, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22117868HCID 22117868, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 10 g of 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-(3-nitrophenyl)-1,8(2H,5H)-acridinedione in 190 ml of ethanol and 100 ml of 1M hydrochloric acid was hydrogenated at atmospheric temperature and pressure in the presence of 0.5 g of 10% palladium on carbon catalyst. When hydrogen uptake had ceased, the catalyst was removed by filtration and the filtrate evaporated. The residue was dissolved in water (20 ml) and the solution made alkaline by addition of excess 1M sodium carbonate solution. The precipitated solid was filtered off, washed with water and dried giving 9.0 g of 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-(3-aminophenyl)-1,8(2H,5H)-acridinedione as a pale brown solid; mass spectrum (ESP) m/e 365 [M+H]+.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in water (20 ml)
  4. additionby addition of excess 1M sodium carbonate solution
  5. filtrationThe precipitated solid was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-5880e5ca73c448ecb377f21cfca281af
Source dataset
uspto-grants-1999_10
Patent number
US05969139

Reaction notes

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