Pyridinium chloride → HCID 44412034, compound

HRID 642788Notes

Reaction equation

HRID 642788 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[C:11]1[C:10]3[CH:17]=[CH:18][CH:19]=[N:20][C:9]=3[S:8][CH2:7][C:6]2=1.Cl.N1C=CC=CC=1>>[CH3:16][N:12]1[C:11]2[C:10]3[CH:17]=[CH:18][CH:19]=[N:20][C:9]=3[S:8][CH2:7][C:6]=2[C:5]2[C:13]1=[CH:14][CH:15]=[C:3]([OH:2])[CH:4]=2

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 596760788-Methoxy-11-methyl-6,11-dihydro-5-thia-4,11-diaza-benzo[a]fluorene

Product 1

HCID 44412034HCID 44412034, compound

Conditions

Temperature
180 °C

Procedure

A mixture of 8-methoxy-11-methyl-6,11-dihydro-5-thia-4,11-diaza-benzo[a]fluorene (100 mg, 0.355 mmoL) and pyridine HCl salt (410 mg, 3.55 mmoL) was sealed in a tube and heated to 180° C. for 2 hours. The reaction mixture was cooled and the residue was partitioned between water and EtOAc. The EtOAc layer was washed with saturated NaHCO3, water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material (the oil) was then purified by column chromatography (silica gel, hexanes:EtOAc 1:1 as eluent) to yield the title compound as a white solid.

Workup

  1. customwas sealed in a tube
  2. temperatureThe reaction mixture was cooled
  3. customthe residue was partitioned between water and EtOAc
  4. washThe EtOAc layer was washed with saturated NaHCO3, water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown oil
  9. customThe crude material (the oil) was then purified by column chromatography (silica gel, hexanes:EtOAc 1:1 as eluent)

Sources & evidence

ORD record
ord-c621b7b37bce48409d90ee8a4a17c15c
Source dataset
uspto-grants-2010_04
Patent number
US07696239B2

Reaction notes

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