HCID 178418361, compound → HCID 178507371, compound

HRID 1199729Notes

Reaction equation

HRID 1199729 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:18]4[NH:22][N:21]=[N:20][N:19]=4)[CH:12]=3)[C:7](=[O:23])[C:6]=2[CH:5]=1)([O-])=O.[H][H]>C(=O)(O)[O-].[Na+].O.[Pd]>[NH2:1][C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:18]4[NH:22][N:21]=[N:20][N:19]=4)[CH:12]=3)[C:7](=[O:23])[C:6]=2[CH:5]=1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178514931HCID 178514931, compound

Product 1

HCID 178507371HCID 178507371, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The nitroxanthone from step (B) (1.55 g) was dissolved in a solution of sodium bicarbonate (0.42 g) in water (150 ml) with warming. To the solution was added 10% palladium on carbon catalyst and the solution hydrogenated at room temperature and atmospheric pressure for 4 hr, during which time hydrogen uptake was measured as 440 ml. The solution was filtered and the filtrate acidified with twice-normal hydrochloric acid solution. The amino-compound was filtered from the warmed mixture, washed well with water and dried to yield 0.98 g, mpt. 296°-297° C. with decomposition.

Workup

  1. temperaturewith warming
  2. customhydrogenated at room temperature
  3. filtrationThe solution was filtered
  4. filtrationThe amino-compound was filtered from the warmed mixture
  5. washwashed well with water
  6. customdried
  7. customto yield 0.98 g, mpt
  8. custom296°-297° C.

Sources & evidence

ORD record
ord-45e7de730fea48d4b1b68550c76306f3
Source dataset
uspto-grants-1990_02
Patent number
US04902701

Reaction notes

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