6-Aminohexanoic Acid → 9-(5-Carboxypentylamino)acridine

HRID 1975899Notes

Reaction equation

HRID 1975899 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].O([C:17]1[C:18]2[C:23]([N:24]=[C:25]3[C:30]=1[CH:29]=[CH:28][CH:27]=[CH:26]3)=[CH:22][CH:21]=[CH:20][CH:19]=2)C1C=CC=CC=1.CCOCC>C1(O)C=CC=CC=1>[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:17]1[C:18]2[C:23]([N:24]=[C:25]3[C:30]=1[CH:29]=[CH:28][CH:27]=[CH:26]3)=[CH:22][CH:21]=[CH:20][CH:19]=2)([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 3283Diethyl EtherHCID 1006409-Phenoxyacridine

Product 1

HCID 1898379-(5-Carboxypentylamino)acridine

Reagents, catalysts & solvents 1

HCID 996PhenolSolvent

Conditions

Temperature
120 °C

Procedure

6-Aminohexanoic acid (1.47 g, 11.2 mmol) was added to a solution of 9-phenoxyacridine (2.7 g, 10 mmol) in phenol (15 g). The suspension was stirred at 120° C. for 2 h. The solution was cooled to room temperature and poured into ether whereby the product precipitated as a yellow-green solid. It was triturated with hot ethanol, filtered then washed with ethanol, giving crude 9-(5-carboxypentyl) Aminoacridine. Yield 2.4 g (78%).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customprecipitated as a yellow-green solid
  3. customIt was triturated with hot ethanol
  4. filtrationfiltered
  5. washthen washed with ethanol

Sources & evidence

ORD record
ord-b4e1721414624cb6a9227bbd58584e05
Source dataset
uspto-grants-2001_05
Patent number
US06225052B1

Reaction notes

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