5-Bromo-9,10-dihydro-9-oxo-4-acridinecarboxylic acid → HCID 10851866, compound

HRID 1952876Notes

Reaction equation

HRID 1952876 reaction equation
[Br: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>[Br: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 232998825-Bromo-9,10-dihydro-9-oxo-4-acridinecarboxylic acid

Product 1

HCID 10851866HCID 10851866, compoundYield 70%

Reagents, catalysts & solvents 1

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

Procedure

Reduction of the known [Rewcastle and Denny, Synthesis, 1985, 217] 5-bromo-9-oxoacridan-4-carboxylic acid as above gave 5-bromoacridine-4-carboxylic acid (70%), mp (MeOH/H2O) 327° C. (dec). 1H NMR [(CD3)2SO] δ 7.71 (dd, J=8.3, 7.4 Hz, 1 H, H-2), 7.94 (dd, J=8.4, 7.1 Hz, 1 H, H-7), 8.40 (dd, J=8.7, 0.8 Hz, 1 H, ArH), 8.50 (dd, J=7.3, 1.0 Hz, 1 H, ArH), 8.64 (dd, J=8.3, 1.3 Hz, 1 H, ArH), 8.85 (dd, J=7.1, 1.3 Hz, 1 H, ArH), 9.66 (s, 1 H, H-9), 16.77 (br s, 1 H, COOH). Anal. (C14H8BrNO2) C, H, N, Br.

Sources & evidence

ORD record
ord-f33f303b6d484f589527214a41af27ad
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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