Water → 1h-Isoindol-1-one,2,3-dihydro-5-(4-nitrophenoxy)-

HRID 1768286Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7]2.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.O>CN(C=O)C>[C:9]1(=[O:13])[C:10]2[C:6](=[CH:5][C:4]([O:3][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[CH:12][CH:11]=2)[CH2:7][NH:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a slurry of NaH (0.39 g, 16.1 mmol) in DMF at 0° C. was added 5-hydroxyisoindolin-1-one (2.0 g, 13.4 mmol) in portions. The resulting slurry was allowed to warm to room temp. and was stirred for 45 min., then 4-fluoro-1-nitrobenzene was added and then mixture was heated at 70° C. for 3 h. The mixture was cooled to 0° C. and treated with water dropwise until a precipitate formed. The resulting solids were collected to give 4-(1-isoindolinon-5-yloxy)-1-nitrobenzene as a dark yellow solid (3.23 g, 89%): TLC (100% EtOAc) Rf 0.35. Step 3. Synthesis of 4-(1-oxoisoindolin-5-yloxy)aniline

Workup

temperatureto warm to room temp.
temperatureThe mixture was cooled to 0° C.
customformed
customThe resulting solids were collected

Sources & evidence

ORD record: ord-40f943e2d39b4f92880d55f2af1ddfad
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235576B1

Reaction notes

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