3,6-dibromo-9-methyl-1-nitro-9h-carbazole → HCID 22280812, compound

HRID 359667Notes

Reaction equation

HRID 359667 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:17]([O-])=O)[C:5]2[N:6]([CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.[H][H]>CO.[Pd]>[NH2:17][C:4]1[C:5]2[N:6]([CH3:16])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 2587513,6-dibromo-9-methyl-1-nitro-9h-carbazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 22280812HCID 22280812, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3,6-Dibromo-9-methyl-1-nitrocarbazole (10 g) was dissolved in 300 ml of methanol. To the solution was added 50 g of Rexyn™ (OH-) form) and, under an atmosphere of carbon dioxide, 2 g of 5% Pd/C. The vessel was charged with 44.5 psi of H2. During the course of the reaction the hydrogen pressure dropped to 32.8 psi (100% H2 uptake). The crude reaction mixture was filtered and the clear solution was evaporated with a rotary evaporator using a vacuum pump and a water bath at 20° C. to give a white solid, m.p. 90°-92° C. Yield 2.77 g (54.3%). The product decomposed readily in air to a red solid.

Workup

  1. additionTo the solution was added 50 g of Rexyn™ (OH-) form) and, under an atmosphere of carbon dioxide
  2. additionThe vessel was charged with 44.5 psi of H2
  3. additiondropped to 32.8 psi (100% H2 uptake)
  4. customThe crude reaction mixture
  5. filtrationwas filtered
  6. customthe clear solution was evaporated with a rotary evaporator
  7. customat 20° C.
  8. customto give a white solid, m.p. 90°-92° C

Sources & evidence

ORD record
ord-eb2516fb60854da59914f20a056d753c
Source dataset
uspto-grants-1991_03
Patent number
US05002856

Reaction notes

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