Acetic Acid → HCID 86587851, compound

HRID 1375316Notes

Reaction equation

[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([O:17][C:18]2[C:23]([Br:24])=[CH:22][C:21]([CH2:25][CH2:26][C:27]([O:29]CC4C=CC=CC=4)=[O:28])=[CH:20][C:19]=2[Br:37])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.Br>O>[CH:11]1[C:12]2[C:7](=[N:6][C:5]3[C:14]([C:13]=2[C:15]([O:17][C:18]2[C:19]([Br:37])=[CH:20][C:21]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:22][C:23]=2[Br:24])=[O:16])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2,6-dibromo-4-(2-benzyloxycarbonylethyl)-phenyl acridine-9-carboxylate (191 mg, 0.309 mmol), glacial acetic acid (20 ml) and 48% hydrobromic acid (5 ml) was heated at 100° C. for 3 h and then cooled. The mixture was added to water (100 ml) and extracted with 20% methanol in chloroform (100 ml×4). The organic extracts were combined and evaporated and the residue was suspended in chloroform (50 ml) and neutralised with a slight excess of triethylamine. The mixture was washed with water (70 ml×3), and the organic layer was dried over sodium sulphate and evaporated to dryness. The residue was recrystallised from CHCl3 to give the desired product (115 mg, 74%.), mp 240–2° C. FAB-MS m/z 529 [M+, 75%], 511 [10], 486 [10], 207 [100].

Workup

temperaturecooled
extractionextracted with 20% methanol in chloroform (100 ml×4)
customevaporated
washThe mixture was washed with water (70 ml×3)
dry with materialthe organic layer was dried over sodium sulphate
customevaporated to dryness
customThe residue was recrystallised from CHCl3

Sources & evidence

ORD record: ord-a85d76e1da3d4daa90387f11341a2fcb
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169554B2

Reaction notes

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