Sodium Hydroxide → 9-oxo-10H-acridine-3-carboxylic Acid
Reaction equation
[C:1]1([NH:7][C:8]2[C:9]([C:17]([OH:19])=O)=[CH:10][CH:11]=[C:12]([CH:16]=2)[C:13]([OH:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>>[O:19]=[C:17]1[C:9]2[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:16][C:8]=2[NH:7][C:1]2[C:2]1=[CH:3][CH:4]=[CH:5][CH:6]=2Participants
Conditions
- Temperature
- 165 °C
Procedure
To a round bottom flask containing polyphosphoric acid (35 g) at 165° C. was added finely ground compound 1B (3.0 g, 1.17 mmol) over 10 min. After the addition was complete, the reaction mixture was stirred for 30 min at 165° C. HPLC indicated that the reaction was complete. While at 165° C., the mixture was slowly added to a mixture of ice and sodium hydroxide. The pH was adjusted to 3.0 with additional sodium hydroxide, and the resulting mixture was filtered through a medium porosity fritted funnel to give a yellow paste which was rinsed with MeOH and DCM into a round bottom flask. The organic solvents were removed under reduced pressure and the residue was azeotripic evaporated several times with MeOH and DCM to give 2.75 g (98%) of compound 1C as a yellow solid. HPLC retention time=2.45 min. (Condition A) and LC/MS M++1=240+. 1H-NMR (500 MHz, DMSO-d6) δ 13.13 (bs, 1H), 11.96 (s, 1H), 8.31 (d, J=8.42 Hz, 1H), 8.24 (d, J=8.20 Hz, 1H), 8.18 (s, 1H), 7.77 (t, J=7.55 Hz, 1H), 7.72 (d, J=8.42 Hz, 1H), 7.55 (d, J=8.20 Hz, 1H), 7.30 (t, J=7.55 Hz, 1H).
Workup
- additionAfter the addition
- filtrationthe resulting mixture was filtered through a medium porosity fritted funnel
- customto give a yellow paste which
- washwas rinsed with MeOH and DCM into a round bottom flask
- customThe organic solvents were removed under reduced pressure
Sources & evidence
- ORD record
- ord-f81a1856990e4071aa8be054b52aae16
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312209B2
Reaction notes
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