ChemicalBook CAS DataBase List 4-PROPOXYANILINE

4-PROPOXYANILINE synthesis

13synthesis methods

Product Name:4-PROPOXYANILINE
CAS Number:4469-80-1
Molecular formula:C9H13NO
Molecular Weight:151.21

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4469-80-1
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Yield:4469-80-1 98%

Reaction Conditions:

with hydrogen;10% palladium on activated carbon in ethanol;ethyl acetate; under 1034.32 - 1965.21 Torr; for 0.5 h;

Steps:

A.147 Example 147; N-(4-propoxyphenyl)-N'-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]urea.

1-(Allyloxy)-4-nitrobenzene (0.51 g, 2.9 mmol) is dissolved in EtOH (50 mL), 10% Pd/C catalyst is added as a slurry in EtOAc and the mixture put on the Parr apparatus in the presence of H2 (38 psi to 20 psi) for 0.5 h. The reaction mixture is filtered over Celite to remove the catalyst and the solvent is removed to give the 4-propyloxyaniline (423 mg, 98% yield) as a brown oil. 4-Propyloxyaniline (0.42 g, 2.8 mmol) is added dropwise as a solution in EtOAc (25 mL) to phosgene (11.8 mL, 20% solution in toluene) in EtOAc (50 mL). After complete addition, the reaction is heated under reflux for 0.5 h. The reaction is cooled to RT and the solvent is removed under reduced pressure to give 1-isocyanato-4-propyloxybenzene (0.49 g, 99% yield) as a brown oil. Example 147 is obtained using the isocyanate according to Method A, making non-critical variations. Yield 8%. HRMS calcd for C13H13F3N4O2S+H 347.0789 found 347.0786.

References:

US2003/236287,2003,A1 Location in patent:Page 35

123-30-8 Synthesis