Pyridinium hydrochloride → HCID 58050245, compound

HRID 1676872Notes

Reaction equation

HRID 1676872 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[N:11]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2.Cl.[NH+]1C=CC=CC=1>O>[CH:22]1[C:23]2[N:11]([C:4]3[C:5]([OH:9])=[CH:6][CH:7]=[CH:8][C:3]=3[OH:2])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 58050238HCID 58050238, compound

Product 1

HCID 58050245HCID 58050245, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9-(2,6-Dimethoxyphenyl)-9H-carbazole (10.00 g) and pyridinium hydrochloride (50.0 g) were placed in the 250 ml round-bottom flask, equipped with magnetic stirrer and immersed in the pre-heated oil bath (230° C., 45 min). The reaction mixture was cooled down to room temperature, diluted with 400 ml water and extracted with ethyl acetate (3×150 ml). Organic fractions were combined, dried over sodium sulfate anhydrous, filtered and evaporated, providing 5.5 g of pure 2-carbazol-9-yl-benzene-1,3-diol. 2-Carbazol-9-yl -benzene-1,3-diol (5.5. g, 20 mmol) and pyridine (6.0 ml) were dissolved in 50 ml DCM (anhydrous) and cooled in the ice bath. Solution of triflic anhydride (6.0 ml) in 20 ml DCM was added dropwise upon intensive stirring, reaction mixture was warmed up to room temperature and stirred overnight. The reaction mixture was washed with water, dried over sodium sulfate, filtered and evaporated, providing crude triflate. Pure material (white solid, 6.0 g) was obtained by column chromatography on silica gel (eluent hexane/ethyl acetate 1/1 mixture).

Workup

  1. customequipped with magnetic stirrer
  2. customimmersed in the pre-heated oil bath (230° C., 45 min)
  3. extractionextracted with ethyl acetate (3×150 ml)
  4. dry with materialdried over sodium sulfate anhydrous
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-87a1210cde9e40518c8200aad150b695
Source dataset
uspto-grants-2011_08
Patent number
US08007927B2

Reaction notes

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