Ammonium Chloride → 3-(3-amino-4-fluorobenzylidene)-3H-isobenzofuran-1-one

HRID 459756Notes

Reaction equation

[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[O:8]2)=[CH:4][C:3]=1[N+:19]([O-])=O.[Cl-].[NH4+]>[Fe].O>[NH2:19][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:2]=1[F:1])[CH:6]=[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[O:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred mixture of the above crude 3-(4-fluoro-3nitrobenzylidene)-3H-isobenzofuran-1-one (23.5 g), industrial methylated spirit (400 ml), water (300 ml) and ammonium chloride (8.81 g, 0.165 mol) was heated to 70° C., and iron powder (46.0 g, 0.824 gatom) was added in portions. When the addition was complete, the stirred mixture was heated at 70° C. for a further 2 hours, then it was filtered while hot through Celite. The collected inorganic solids were washed with hot industrial methylated spirit (6×200 ml), then the filtrate and washings were combined and the solvent was removed in vacuo. The residue was triturated with water (300 ml) and the resulting solid was collected by filtration and dried in vacuo for 24 hours to give crude 3-(3-amino-4-fluorobenzylidene)-3H-isobenzofuran-1-one as a yellow solid, m/z (M+H)+. 256, 100% purity, which was used directly in the next stage.

Workup

additionWhen the addition
temperaturethe stirred mixture was heated at 70° C. for a further 2 hours
filtrationit was filtered while hot through Celite
washThe collected inorganic solids were washed with hot industrial methylated spirit (6×200 ml)
customthe solvent was removed in vacuo
customThe residue was triturated with water (300 ml)
filtrationthe resulting solid was collected by filtration
customdried in vacuo for 24 hours

Sources & evidence

ORD record: ord-395bd31dc99b41bf942731b9f00a0db7
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196085B2

Reaction notes

Loading…