1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 19996034, compound

HRID 2248302Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][N:3]=1.Br[CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22]>CO>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][CH2:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

2-Chloro-5-aminopyridine (12.85 g, 0.1 mol) and N-(2-bromoethyl)phthalimide (25.4 g, 0.1 mol) were stirred together at ambient temperature (20° C.). The resulting mixture was heated to 120° C. and held at that temperature for 30 minutes whilst vigorous stirring was maintained. The mixture was allowed to cool, and when the temperature had reduced to 60° C., methanol (250 ml) was added and stirring was maintained until a homogeneous solution was obtained. The solution was then cooled to ambient temperature (20° C.), silica gel, 230 to 400 US mesh (0.062 mm to 0.037 mm) (50 g) was added and the mixture was evaporated to dryness. The title product, (N-(N-(6-chloro-3-pyridyl)-2-aminoethyl)phthalimide, was isolated from the dried mixture by flash chromatography on a silica column using silica gel, 230 to 400 US mesh (0.062 mm to 0.037 mm), and with 2% w methanol in dichloromethane as eluent, as a buff solid (7 g, 46%).

Workup

temperaturewas maintained
temperatureto cool
customhad reduced to 60° C.
stirringstirring
temperaturewas maintained until a homogeneous solution
customwas obtained
temperatureThe solution was then cooled to ambient temperature (20° C.), silica gel, 230 to 400 US mesh (0.062 mm to 0.037 mm) (50 g)
additionwas added
customthe mixture was evaporated to dryness

Sources & evidence

ORD record: ord-77e4cad140414d229d2f6af1b80cd875
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05039686

Reaction notes

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