Hydrochloric Acid → HCID 178421629, compound

HRID 1911082Notes

Reaction equation

HRID 1911082 reaction equation
[Cl:1][C:2]1[C:18]2[C:6](=[C:7]([CH3:21])[C:8]3[NH:9][C:10]4[CH:11]=[CH:12][C:13]([O:19]C)=[CH:14][C:15]=4[C:16]=3[CH:17]=2)[CH:5]=[CH:4][N:3]=1.Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[C:18]2[C:6](=[C:7]([CH3:21])[C:8]3[NH:9][C:10]4[CH:11]=[CH:12][C:13]([OH:19])=[CH:14][C:15]=4[C:16]=3[CH:17]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178488042HCID 178488042, compound

Product 1

HCID 178421629HCID 178421629, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
140 °C

Procedure

In a 5 ml sealed tube, a mixture of 1-chloro-9-methoxy-5-methyl-6H-pyrido[4,3-b]carbazole (75 mg, 0.25 mMol) (prepared according to J. Chem. Soc. Perkin Trans. 1, 1979, 1706), benzyltriethylammonium chloride (225 mg, 1 mMol) and 37% hydrochloric acid (4 ml) is heated in an oil bath at 140° C. for 24 h. The reaction mixture is then evaporated, under vacuum, then 20 ml of water are added. The medium is then rendered basic by addition of 28% ammonium hydroxide (0.5 ml), and the solid is recovered by low-temperature filtration, then washed with water and dried using a vacuum desiccator, at a temperature of 200° C. for 18 h. 65 mg (90% yield) of Compound 10 are then obtained, the proton NMR spectrum of which is the following:

Workup

  1. customIn a 5 ml sealed tube
  2. customThe reaction mixture is then evaporated, under vacuum
  3. addition20 ml of water are added
  4. additionThe medium is then rendered basic by addition of 28% ammonium hydroxide (0.5 ml)
  5. filtrationthe solid is recovered by low-temperature filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-00d922b52c594cb080a41fbb2279fce8
Source dataset
uspto-grants-2013_12
Patent number
US08604048B2

Reaction notes

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