4'-Hydroxyacetophenone → 4-(4-Acetylphenoxy)-5-nitropyridine

HRID 78340Notes

Reaction equation

[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1>>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:16]2[C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=[CH:12][CH:17]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

Participants

Reactant 2

HCID 74694'-Hydroxyacetophenone

HCID 783082-Chloro-5-nitropyridine

Product 1

HCID 231372284-(4-Acetylphenoxy)-5-nitropyridine

Procedure

Entry 9: 4-Hydroxyacetophenone was reacted with 2-chloro-5-nitropyridine to give 4-(4-acetylphenoxy)-5-nitropyridine according to Method A3, Step 2. According to Method A8, Step 4, 4-(4-acetylphenoxy)-5-nitropyridine was reduced to 4-(4-acetylphenoxy)-5-aminopyridine. 2-Methoxy-5-(trifluoromethyl)aniline was converted to 2-methoxy-5-(trifluoromethyl)phenyl isocyanate according to Method B1. The isocyanate was reacted with 4-(4-acetylphenoxy)-5-aminopyridine according to Method C1a to afford the urea.

Sources & evidence

ORD record: ord-2d685674854f4183955743df43cfbfd2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841330B2

Reaction notes

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