Hydrochloric Acid → 6-(9-oxo-9H-acridin-4-carboxamido)hexanoic acid

HRID 1662929Notes

Reaction equation

HRID 1662929 reaction equation
[C:1]([C:4]1[C:17]2[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:18])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([OH:3])=O.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([OH:60])=[O:59].Cl>O.CO.CN(C)C=O>[O:18]=[C:9]1[C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([C:1]([NH:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([OH:60])=[O:59])=[O:3])[C:17]=2[NH:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5646-Aminohexanoic AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 35607584-Carboxy-9-acridanone

Product 1

HCID 666633786-(9-oxo-9H-acridin-4-carboxamido)hexanoic acidYield 62.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Carboxyacridone (2.15 g, 9 mmol), was mixed with N,N-dimethylformamide (15 ml) and N,N-diisopropylethylamine (1.6 ml, 9.2 mmol) and stirred under nitrogen to give a deep yellow solution. To this was added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.5 g, 9 mmol) and stirring continued for 2 hrs. During this time a thick yellow precipitate formed. 6-Aminohexanoic acid (1.45 g, 11 mmol) was then added and stirring continued overnight. Reverse phase chromatographic analysis (C18) (methanol:water, 80:20) indicated two spots at Rf=0.75 and Rf=0.55. The reaction mixture was then poured into 0.25M aqueous HCl (200 ml) and the precipitated product collected by vacuum filtration, washing with more dilute HCl and water. The still-damp solid was recrystallized from ethanol/water and dried under vacuum over phosphorus pentoxide to give 6-(9-oxo-9H-acridin-4-carboxamido)hexanoic acid (1.97 g, 62%). λmax (EtOH)=408, 390, 256 nm. δH (300 MHz, DMSO-d6) 1.35-1.65 (6H, m), 2.24 (2H, t), 3.40 (2H, t), 7.26-7.39 (2H, m), 7.74-7.77 (2H, m), 8.21-8.28 (2H, m), 8.44 (2H, app.d), 9.00 (1H, broad t, amide), 12.02 (broad s, D20 exch.) and 12.49 (broad s, D20 exch.). Mass spectrum: MALDI-TOF, m/z=353.15, M=353.15 for C20H21N2O4. Melting Point=218° C.

Workup

  1. customto give a deep yellow solution
  2. stirringstirring
  3. customDuring this time a thick yellow precipitate formed
  4. stirringstirring continued overnight
  5. filtrationthe precipitated product collected by vacuum filtration
  6. washwashing with more dilute HCl and water
  7. customThe still-damp solid was recrystallized from ethanol/water
  8. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-103d7b38137e4b5180a06a4fcddd4439
Source dataset
uspto-grants-2011_10
Patent number
US08034558B2

Reaction notes

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