HCID 13763252, compound → HCID 10685534, compound

HRID 1952879Notes

Reaction equation

HRID 1952879 reaction equation
[C:1]1([C:7]2[CH:20]=[C:19]3[C:10]([NH:11][C:12]4[C:13]([C:22]([OH:24])=[O:23])=[CH:14][CH:15]=[CH:16][C:17]=4[C:18]3=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(C)=O>[C:1]1([C:7]2[CH:20]=[C:19]3[C:10]([N:11]=[C:12]4[C:17](=[CH:18]3)[CH:16]=[CH:15][CH:14]=[C:13]4[C:22]([OH:24])=[O:23])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 13763252HCID 13763252, compound

Product 1

HCID 10685534HCID 10685534, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Reduction of the known [Denny et al., J. Med. Chem., 1987, 30, 658] 7-phenyl-9-oxoacridan-4-carboxylic acid as above gave 7-phenylacridine-4-carboxylic acid (69%), mp (acetone) 239-241° C. 1H NMR [(CD3)2SO] δ 7.49 (t, J=7.3 Hz, 1 H, H-4'), 7.60 (t, J=7.3 Hz, 2 H, H-3' and H-5'), 7.86 (dd, J=8.4, 7.1 Hz, 1 H, H-2), 7.96 (d, J=7.3 Hz, 2 H, H-2' and H-6'), 8.43 (br s, 2 H, H-6 and H-8), 8.58 (dd, J=8.5, 1.2 Hz, 1 H, H-1), 8.64 (br s, 1 H, H-5), 8.74 (br d, J=7.1 Hz, 1 H, H-3), 9.56 (s, 1 H, H-9), 16.93 (br s, 1 H, COOH). Anal. (C20H13NO2) C, H, N.

Sources & evidence

ORD record
ord-71b051891b3b4fdc9fffd6a75da29137
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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