4-Nitrophenol → 4-[(2-Methoxyethoxy)methoxy]aniline

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Reaction Steps

For the synthesis of an acetaminophen FP tracer having an acyclic linker, p-Nitrophenol was protected as a methoxyethoxy methyl ether (FIG. 6). The nitro group was reduced to an amino in the presence of ammonium formate and 10% Pd--C in ethanol to yield 4-[(2-methoxyethoxy)methoxy]benzenamine (22). The amino group was succinylated and the acid derivative produced was coupled to 4'-aminomethylfluorescein. Deprotection of the methoxyethoxy ether (27) in the presence of trifluoroacetic acid yielded rac-4-[[[3',6'-dihydroxy-3-oxospiro-[isobenzofuran-1(3H),9'-[9H] xanthen]-4'-yl)methyl]amino]-N-(4-hydroxyphenyl)-4-oxobutamide (28) .

Provenance & Evidence