Acetaminophen → 5-(3-Acetamidophenoxy)-2-nitroaniline

HRID 1294054Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(NC1C=CC(O)=CC=1)(=O)C.[N+](C1C=CC(O[C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[C:33]([N+:38]([O-:40])=[O:39])[CH:32]=2)=CC=1)([O-])=O>>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][C:37]1[CH:31]=[CH:32][C:33]([N+:38]([O-:40])=[O:39])=[C:34]([CH:36]=1)[NH2:35])(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 1983Acetaminophen

HCID 121243-Hydroxyacetanilide

HCID 12032722Benzenamine, 2-nitro-4-(4-nitrophenoxy)-

Product 1

HCID 177550365-(3-Acetamidophenoxy)-2-nitroaniline

Procedure

3-Acetamidophenol was utilized instead of 4-acetamidophenol, according to the same procedure for Intermediate 1 to prepare Intermediate 1A: MS m/e 286 (M−1).

Sources & evidence

ORD record: ord-69df96b0f4d64a5a8d0a426fe476b240
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238813B2

Reaction notes

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