phenazin-1-ylmethanol synthesis

6synthesis methods

Product Name:phenazin-1-ylmethanol
CAS Number:1082-79-7
Molecular formula:C13H10N2O
Molecular Weight:210.23

1019-54-1
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1082-79-7
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Yield:1082-79-7 98.4%

Reaction Conditions:

with sodium carbonate in water;N,N-dimethyl-formamide at 80; for 2 h;Solvent;Reagent/catalyst;Temperature;Time;Concentration;

Steps:

Synthesis of 1-phenazinemethanol (II)

Compound III (10 g, 36.6 mmol) was dissolved in the mixture of DMF (80mL) and 0.5 % Na2CO3 aqueous solution (88 mL) in a three necked flask equipped with an efficient reflux condenser. The mixture was heated at 80 C for 2 h under stirring. Then, the mixture was cooled and poured into water (100 mL) and extracted with EtOAc (50 mL ~ 3). The obtained EtOAc extract was washed with 0.2 N HCl (30 mL ~ 2) and finally washed with saturated NaCl solution. After drying with anhydrous Na2SO4, the organic layer was concentrated in vacuum to get the crude product. The residue was purified by recrystallization to obtain II (7.6 g, 98.4 %) as yellow solid. m.p. 132-134 C; 1H NMR (CDCl3, 400 MHz) : 4.50 (t, J = 6.4, 1H), 5.33 (d,J = 6.3, 2H), 7.72-7.78 (m, 2H), 7.84 (t, J = 4.1, 2H), 8.14-8.24 (m, 3H); 13C NMR (CDCl3, 100 MHz) : 143.7, 142.4,141.9, 138.8, 138.7, 130.7, 130.6, 130.3, 129.6, 129.5, 129.2,128.2, 63.9; ESI-MS m/z: 211.1 (100 %).

References:

Zhan;Zhu;Huang;Liu;Zhu [Asian Journal of Chemistry,2015,vol. 27,# 9,p. 3355 - 3360]