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

HRID 1603233Notes

Reaction equation

HRID 1603233 reaction equation
CC([NH:4][C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=O.[CH:12]1C([N+]([O-])=O)=CC=C(O)C=1.CO[O:24][CH2:25][CH2:26][O:27][CH3:28].C([O-])=O.[NH4+]>C(O)C>[CH3:28][O:27][CH2:26][CH2:25][O:24][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([NH2:4])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 1983AcetaminophenHCID 2723923Ammonium formateHCID 21712034Methoxyethoxy methyl ether

Product 1

HCID 131356894-[(2-Methoxyethoxy)methoxy]aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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) .

Sources & evidence

ORD record
ord-c5d829886970468aa1b833b7ca66e95e
Source dataset
uspto-grants-1999_11
Patent number
US05986094

Reaction notes

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