Beta-Alanine → 3-(Acridin-9-ylamino)propanoic acid

HRID 1975898Notes

Reaction equation

HRID 1975898 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].O([C:14]1[C:15]2[C:20]([N:21]=[C:22]3[C:27]=1[CH:26]=[CH:25][CH:24]=[CH:23]3)=[CH:19][CH:18]=[CH:17][CH:16]=2)C1C=CC=CC=1.CCOCC>C1(O)C=CC=CC=1>[C:4]([CH2:3][CH2:2][NH:1][C:14]1[C:15]2[C:20]([N:21]=[C:22]3[C:27]=1[CH:26]=[CH:25][CH:24]=[CH:23]3)=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 3283Diethyl EtherHCID 1006409-Phenoxyacridine

Product 1

HCID 31583193-(Acridin-9-ylamino)propanoic acid

Reagents, catalysts & solvents 1

HCID 996PhenolSolvent

Conditions

Temperature
120 °C

Procedure

β-Alanine (1 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 and then washed with ethanol, giving crude 9-(2-carboxyethyl)aminoacridine. Yield 1.9 g (71%).

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. washwashed with ethanol

Sources & evidence

ORD record
ord-b692b1cb03e541c3a4a9b1b8d3cf0a59
Source dataset
uspto-grants-2001_05
Patent number
US06225052B1

Reaction notes

Loading…