Maleic Anhydride → 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-2-iodo-benzonitrile

HRID 966931Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([I:10])[CH:3]=1.[C:11]1(=O)[O:16][C:14](=[O:15])[CH:13]=[CH:12]1>C(O)(=O)C>[O:15]=[C:14]1[CH:13]=[CH:12][C:11](=[O:16])[N:1]1[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([I:10])[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Compound 489C (3.97 g, 16.3 mmol) and maleic anhydride (2.41 g, 24.4 mmol) were refluxed in glacial acetic acid (15 mL) for 5 h. The reaction was cooled to 25° C. and then poured onto ice (100 mL). The resulting precipitate was isolated by filtration and washed with water (2×25 mL) and dried under vacuum to yield 4.78 g (90%) of compound 489D as a tan solid. HPLC: 82% at 2.68 min (retention time) C Shimadzu VP-ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 min containing 0.1% trifluoroacetic acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 325.04 [M+H]+.

Workup

additionpoured onto ice (100 mL)
customThe resulting precipitate was isolated by filtration
washwashed with water (2×25 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-4fa2795197c040c78b720b9e7bff480a
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06953679B2

Reaction notes

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