ChemicalBook CAS DataBase List 4-METHOXY-O-PHENYLENEDIAMINE

4-METHOXY-O-PHENYLENEDIAMINE synthesis

9synthesis methods

Product Name:4-METHOXY-O-PHENYLENEDIAMINE
CAS Number:102-51-2
Molecular formula:C7H10N2O
Molecular Weight:138.17

96-96-8

102-51-2

General procedure for the synthesis of 4-methoxy-o-phenylenediamine from 4-methoxy-2-nitroaniline: 360 mg (2.14 mmol) of 4-methoxy-2-nitroaniline was placed in a hydrogenation reactor and 65 mL of ethanol was added. Subsequently, a small amount of 10% palladium/activated carbon catalyst was added and the reaction mixture was hydrogenated at room temperature under 50 Psi hydrogen pressure for 24 hours. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated on a rotary evaporator to afford 4-methoxyphthalimide (294 mg, 2.12 mmol, 99% yield) as a dark purple oil. The product was characterized by 1HNMR (CDCl3): δ 6.64 (d, J = 8.7 Hz, 1H), 6.35-6.30 (m, 1H), 6.26 (d, J = 8.7 Hz, 1H), 3.52 (s br, 2H), 3.07 (s br, 2H).

96-96-8
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102-51-2
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Yield:102-51-2 99%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in ethanol at 20; under 2585.81 Torr; for 24 h;

Steps:

32 Synthesis of TZ10-55
Approximately 360 mg (2.14 mmol) of 4-methoxy-2-nitroanniline was placed in a hydrogenator and 65 mL ethanol was added. A pinch of 10% palladium on activated carbon was added and the reaction mixture hydrogenated at room temperature under 50 Psi pressure for 24 hrs. The reaction mixture was filtered and concentrated on rotovap to give TZ10-55 as dark purple oil (294 mg, 2.12 mmol, 99%). ¹HNMR (CDCl₃): δ 6.64 (d, J=8.7 Hz, 1H), 6.35-6.30 (m, 1H), 6.26 (d, J=8.7 Hz, 1H), 3.52 (s br, 2H), 3.07 (s br, 2H).

References:

Washington University;Tu, Zhude;Mach, Robert;Yu, Lihai;Kotzbauer, Paul US2013/315825, 2013, A1 Location in patent:Paragraph 0220

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