HCID 23299888, compound → HCID 10514240, compound

HRID 1952880Notes

Reaction equation

HRID 1952880 reaction equation
[F:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[C:8]([C:17]([OH:19])=[O:18])=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]2=O)=[CH:4][CH:3]=1>CO.O>[F:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6]=[C:7]3[C:12](=[CH:13]2)[CH:11]=[CH:10][CH:9]=[C:8]3[C:17]([OH:19])=[O:18])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 23299888HCID 23299888, compound

Product 1

HCID 10514240HCID 10514240, compoundYield 95%

Reagents, catalysts & solvents 1

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

Procedure

Reduction of the known [Atwell et al., J. Med. Chem., 1987, 30, 658] 7-fluoro-9-oxoacridan-4-carboxylic acid as above gave 7-fluoroacridine-4-carboxylic acid (95%), mp (MeOH/H2O) 267-268° C. 1H NMR [(CD3)2SO] δ 7.87 (dd, J=8.4, 7.0 Hz, 1 H, H-2), 8.01 (ddd, J=9.5, 8.5, 2.3 Hz, 1 H, H-6), 8.13 (dd, J=9.3, 2.8 Hz, 1 H, H-8), 8.45 (dd, J=9.6, 5.3 Hz, 1 H, H-5), 8.54 (dd, J=8.5, 1.3 Hz, 1 H, H-1), 8.73 (dd, J=6.9, 1.4 Hz, 1 H, H-3), 9.47 (s, 1 H, H-9), 16. 53 (br s, 1 H, COOH). Anal. (C14H8FNO2) C, H, N, F.

Sources & evidence

ORD record
ord-83413312b8f747639c057a814100bdd1
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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