1,2,3,4-Tetrahydro-9-methylcarbazol-4-one Chemical Properties

Melting point:

199.0 to 203.0 °C

Boiling point:

383.5±11.0 °C(Predicted)

Density 

1.21±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)

form 

solid

color 

White to Light yellow

BRN 

153862

InChI

InChI=1S/C13H13NO/c1-14-10-6-3-2-5-9(10)13-11(14)7-4-8-12(13)15/h2-3,5-6H,4,7-8H2,1H3

InChIKey

HHJUJCWZKJMCLC-UHFFFAOYSA-N

SMILES

N1(C)C2=C(C=CC=C2)C2=C1CCCC2=O

CAS DataBase Reference

27387-31-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-52/53-25

Safety Statements 

22-24/25-61-45

RIDADR 

UN 2811 6.1 / PGIII

HS Code 

2933998090

1,2,3,4-Tetrahydro-9-methylcarbazol-4-one Usage And Synthesis

Chemical Properties

1,2,3,4-Tetrahydro-9-methylcarbazol-4-one is Off-White Solid

Uses

1,2,3,4-Tetrahydro-9-methylcarbazol-4-one is used in the preparation of 5-HT3 modulators useful in the treatment and prevention of 5-HT3 receptor-mediated diseases. 1,2,3,4-Tetrahydro-9-methylcarbazol-4-one is an impurity of Ondansetron (O655000).

Synthesis

The reaction was carried out in N,N-dimethylformamide (5.0 mL) at reflux for 1.0 h with 2,3-dihydro-1H-carbazol-4(9H)-one (1.0 mmol) and N,N-dimethylformamide dimethyl acetal (10 mmol). After completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate (2 x 25 mL). The organic layer was separated and washed with saturated brine solution and subsequently dried over anhydrous Na2SO4. The solvent was removed by concentration under reduced pressure and the resulting solid was recrystallized from ethanol to give white acicular crystals in 71% yield, melting point 188-190 °C. IR (cm-1 ): 1695 (C=O). 1H NMR (400 MHz, CDCl3) δ: 2.24-2.27 (t, 2H, CH2, J = 6.28 Hz), 2.56-2.59 (t, 2H, CH2, J = 6.0 Hz), 2.56-2.59 (t, 2H, CH2, J = 6.0 Hz). CH2, J = 6.0 Hz), 2.91-2.94 (t, 2H, CH2, J = 6.21 Hz), 3.70 (s, 3H, NCH3), 7.27-7.30 (m, 3H, Ph), 8.24-8.26 (m, 1H, Ph). Calculated elemental analysis (C13H13NO): C, 78.36; H, 6.58; N, 7.03%. Measured values: C, 78.29; H, 6.49; N, 6.92%.

References

[1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53B, # 12, p. 1606 - 1610
[2] Journal of Molecular Structure, 2014, vol. 1080, p. 137 - 144
[3] Russian Chemical Bulletin, 2005, vol. 54, # 8, p. 1887 - 1891

1,2,3,4-Tetrahydro-9-methylcarbazol-4-one(27387-31-1)Related Product Information

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