Aniline → 5-hydroxy-2-phenylisoindole-1,3-dione

HRID 1464010Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=O)[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>>[OH:1][C:2]1[CH:3]=[C:4]2[C:11](=[O:13])[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6](=[O:8])[C:5]2=[CH:9][CH:10]=1

Participants

Reactant 3

HCID 6115Aniline

HCID 118814-Hydroxyphthalic acid

HCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 108238905-hydroxy-2-phenylisoindole-1,3-dione

Procedure

4-Hydroxy-N-phenylphthalimide was synthesized from 4-hydroxyphthalic acid and aniline in the same manner as in Example 1, a). By the reaction of the synthesized compound with trifluoromethanesulfonic anhydride, 4-(N-phenylphthalimide)-yl-triflate (NPhITf) was synthesized.

Workup

customwas synthesized

Sources & evidence

ORD record: ord-2b92428983f34882958abb1a9d0f76da
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05302725

Reaction notes

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