Aniline → 6-Nitro-2-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one

HRID 1023690Notes

Reaction equation

CO[C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13]Br.[CH3:16][O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.NC1C=CC=CC=1>>[N+:10]([C:8]1[CH:9]=[C:4]2[C:5]([CH2:13][N:22]([C:21]3[CH:23]=[CH:24][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[C:3]2=[O:15])=[CH:6][CH:7]=1)([O-:12])=[O:11]

Participants

Reactant 3

HCID 6115Aniline

HCID 7732P-Anisidine

HCID 14552709Methyl 2-(bromomethyl)-5-nitrobenzoate

Product 1

HCID 670452946-Nitro-2-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one

Procedure

By using 2-bromomethyl-5-nitrobenzoic acid methyl ester and 4-methoxyaniline instead of 2-bromomethyl-6-nitro-benzoic acid methyl ester and aniline used in Example 25, synthesis was performed in the same manner as that of Example 25 to obtain 6-nitro-2-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one.

Workup

customused in Example 25, synthesis

Sources & evidence

ORD record: ord-73d3fb4aa363476d8bdab05410a57576
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722723B2

Reaction notes

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