Hydrogen Bromide → 9-Phenoxycarbonyl-10-carboxymethylacridinium bromide

HRID 440633Notes

Reaction equation

HRID 440633 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[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.I[CH2:25][C:26]([O:28]C(C)(C)C)=[O:27].C(OCC)C.[BrH:38]>C(O)(=O)C.O>[Br-:38].[O:17]([C:15]([C:13]1[C:12]2[C:7]([N+:6]([CH2:25][C:26]([OH:28])=[O:27])=[C:5]3[C:14]=1[CH:1]=[CH:2][CH:3]=[CH:4]3)=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 517916Phenyl acridine-9-carboxylateHCID 11021060Tert-butyl 2-iodoacetate

Product 1

HCID 193649399-Phenoxycarbonyl-10-carboxymethylacridinium bromide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of phenyl acridine-9-carboxylate (100 mg) and t-butyl iodoacetate is stirred and heated at 110° C. for five hours. The resulting solution is poured into diethyl ether (25 ml) and the resulting precipitate isolated by filtration. Part of this precipitate (10 mg) is stirred with 33% hydrobromic acid in acetic acid (1 ml), and heated at 50° C. for two hours. The reaction mixture is poured into water, and the resulting precipitate (ca. 6 mg) isolated. MS: 358, 314, 300, 237, 220, 206.

Workup

  1. customthe resulting precipitate isolated by filtration
  2. temperatureheated at 50° C. for two hours

Sources & evidence

ORD record
ord-ff48499828724ea1af2ccfe2d7352e58
Source dataset
uspto-grants-1996_05
Patent number
US05521103

Reaction notes

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