HCID 178508074, compound → HCID 178507367, compound

HRID 345381Notes

Reaction equation

HRID 345381 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[N:8][NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[N+:11]([O-])=O>C(O)C.Cl.[Pd]>[NH2:1][C:2]1[C:10]2[N:9]=[N:8][NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:11]

Participants

5

Reactant 1

HCID 178508074HCID 178508074, compound

Product 1

HCID 178507367HCID 178507367, compoundYield 117.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A suspension of 4-amino-5-nitrobenzotriazole (0.72 g, 4 mmol) in 100 ml of ethanol and 1 ml of conc. hydrochloric acid was hydrogenated at atmospheric pressure and room temperature for 6 h in the presence of 100 mg of 5% palladium-on-charcoal. The mixture was filtered and the catalyst was washed with about 50 ml of water. The combined filtrate was evaporated to dryness giving 0.70 g of the 4,5-diamino-benzotriazole as an hydrochloride. A solution of the crude diamino compound in 40 ml of 4M hydrochloric acid was refluxed with oxalic acid dihydrate (0.50 g, 4 mmol) for 3 h. The mixture was cooled on ice, and pH was adjusted to 5-6 with 2N sodium hydroxide. The precipitate was filtered off and washed with water and ethanol. It was then dissolved in 10 ml of 2N sodium hydroxide, treated with decolourising charcoal, and filtered. After adjustment to pH 6-7 with 4M hydrochloric acid the reprecipitated product was isolated, washed with water and ethanol, and dried at 100 ° C. affording 0.12 g (15%) of pure title compound; m.p.>300° C.; IR (KBr): 3200-2000, 1670 cm-1 ; 1H-NMR (DMSO-d6) 6.9 (broad s, 3H, NH+2OH); 7.03 (d,J=8 Hz, 1H, ArH); 7.43 (d,J=8 Hz,1H, ArH).

Workup

  1. filtrationThe mixture was filtered
  2. washthe catalyst was washed with about 50 ml of water
  3. customThe combined filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-b10fbb04db2e44c0b0f2c80dcac67530
Source dataset
uspto-grants-1991_10
Patent number
US05057516

Reaction notes

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