ChemicalBook CAS DataBase List 2-METHOXY-9H-CARBAZOLE

2-METHOXY-9H-CARBAZOLE synthesis

12synthesis methods

Product Name:2-METHOXY-9H-CARBAZOLE
CAS Number:6933-49-9
Molecular formula:C13H11NO
Molecular Weight:197.23

20013-55-2
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6933-49-9
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Yield:6933-49-9 93%

Reaction Conditions:

with triethyl phosphite for 16 h;Heating / reflux;

Steps:

11
Synthesis example 11 2-methoxycarbazole 8.36 g (36.7 mmol) 4'-methoxy-2-nitro-1,1'-biphenyl in 40 ml triethylphosphite is refluxed during 16 hours in argon atmosphere. The mixture was allowed to cool to room temperature, upon which the product precipitates. Filtration and washing with methanol gave 6.67 g (93 %) of a white solid ¹H NMR (DMSO-d₆): δ11.10 (s, 1H), 8.00 (dd, J=1.5 Hz, J=8 Hz, 1H), 7.8 (d, J=8 Hz, 1H), 7.44 (dd, J=1.5 Hz, J=8 Hz, 1H), 7.30 (dt, J=1.5 Hz, J=8 Hz, 1H), 7.12 (dt, J=1.5 Hz, J=8 Hz, 1H), 6.98 (d, J=1.5 Hz, 1H), 6.78 (dd, J=1.5 Hz, J=8 Hz, 1H), 3.83 (s, 3H). ¹³C NMR (DMSO-d₆): δ 158, 141, 140, 124, 123, 121, 119, 118, 116, 111, 108, 94, 55. mp: 239 °C.

References:

Koninklijke Philips Electronics N.V. EP1838671, 2008, B1 Location in patent:Page/Page column 11; 12

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