HCID 15337384, compound → HCID 15337385, compound

HRID 1952887Notes

Reaction equation

HRID 1952887 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]1[C:7]([C:8]([C:17]([O:19]C)=[O:18])=[CH:9][CH:10]=[CH:11]1)=[N:6]2>CO.O>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]1[C:7]([C:8]([C:17]([OH:19])=[O:18])=[CH:9][CH:10]=[CH:11]1)=[N:6]2

Participants

3

Reactant 1

HCID 15337384HCID 15337384, compound

Product 1

HCID 15337385HCID 15337385, compoundYield 81%

Reagents, catalysts & solvents 1

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

Procedure

Cyclization of this as above, followed by immediate hydrolysis of the crude methyl 6-trifluoromethylacridine-4-carboxylate, gave 6-trifluoromethylacridine-4-carboxylic acid (81%), mp (MeOH/H2O) 244-246° C. 1H NMR [(CD3)2SO] δ 7.93 (t, J=7.9 Hz, 1 H, H-3), 7.98 (dd, J=8.9, 1.5 Hz, 1 H, ArH), 8.56 (d, J=8.8 Hz, 1 H, ArH), 8.60 (d, J=8.5 Hz, 1 H, ArH), 8.79 (dd, J=7.0, 1.1 Hz, 1 H, ArH), 8.86 (s, 1 H, H-5), 9.66 (s, 1 H, H-9).

Sources & evidence

ORD record
ord-ea5f6daeb0a94521b3d0c40a5a226e47
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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