HCID 178510074, compound → HCID 178510041, compound

HRID 379532Notes

Reaction equation

HRID 379532 reaction equation
[C:1]([C:3]1[C:11]2[N:10]=[N:9][NH:8][C:7]=2[C:6]([N+:12]([O-])=O)=[CH:5][CH:4]=1)#[N:2]>CO.[Pd]>[C:1]([C:3]1[C:11]2[N:10]=[N:9][NH:8][C:7]=2[C:6]([NH2:12])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 178510074HCID 178510074, compound

Product 1

HCID 178510041HCID 178510041, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-cyano-7-nitrobenzotriazole (120 mg, 0.63 mmol) in methanol (250 ml) was added 10% Pd/C (1.0 g). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure for 4 hrs. The reaction mixture was flushed with argon and 10% Pd/C (1.0 g) was additionally added and a hydrogen atmosphere was maintained at balloon pressure for 1 hr. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (5%MeOH/CH2Cl2) gave the desired product (95 mg, 94%). 1H NMR (CD3OD): δ7.58 (d, 1H), 6.53 (d, 1H).

Workup

  1. customThe mixture was flushed with argon
  2. customhydrogen was bubbled through the solution for 10 min.
  3. temperaturea hydrogen atmosphere was maintained at balloon pressure for 4 hrs
  4. customThe reaction mixture was flushed with argon and 10% Pd/C (1.0 g)
  5. additionwas additionally added
  6. temperaturea hydrogen atmosphere was maintained at balloon pressure for 1 hr
  7. filtrationThe mixture was filtered through celite
  8. washthe celite was washed with methanol
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d117dfcd9f6a49a99ab5c8c8369b84ec
Source dataset
uspto-grants-2001_10
Patent number
US06300325B1

Reaction notes

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