5-Fluoro-9-oxo-9,10-dihydroacridine-4-carboxylic acid → HCID 10847673, compound

HRID 1952875Notes

Reaction equation

HRID 1952875 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:3]=1[NH:4][C:5]1[C:6]([C:17]([OH:19])=[O:18])=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]2=O>CO.O>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:3]=1[N:4]=[C:5]1[C:10](=[CH:11]2)[CH:9]=[CH:8][CH:7]=[C:6]1[C:17]([OH:19])=[O:18]

Participants

3

Reactant 1

HCID 137632535-Fluoro-9-oxo-9,10-dihydroacridine-4-carboxylic acid

Product 1

HCID 10847673HCID 10847673, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Reduction of the known [Rewcastle and Denny, Synthesis, 1985, 217] 5-fluoro-9-oxoacridan-4-carboxylic acid as above gave 5-fluoroacridine-4-carboxylic acid (90%), mp (MeOH/H2O) 295-298° C. (dec). 1H NMR [(CD3)2SO] δ 7.74-7.80 (m, 1 H, ArH), 7.90-7.96 (m, 2 H, ArH), 8.19 (d, J=8.6 Hz, 1 H, ArH), 8.61 (dd, J=8.6, 1.2 Hz, 1 H. ArH), 8.81 (dd, J=7.0, 1.0 Hz, 1 H, ArH), 9.65 (s, 1 H, H-9). Anal. (C14H8FNO2) C, H, N, F.

Sources & evidence

ORD record
ord-5f5956bc93654689a752b3ca0c33b351
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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