4-(Trifluoromethyl)anthranilic acid → HCID 10569069, compound

HRID 1952886Notes

Reaction equation

HRID 1952886 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH2:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8].I[C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]>CO.O>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([NH:12][C:16]2[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])[CH:4]=1

Participants

4

Reactant 2

HCID 678694-(Trifluoromethyl)anthranilic acidHCID 69132Benzoic acid, 2-iodo-, methyl ester

Product 1

HCID 10569069HCID 10569069, compoundYield 43%

Reagents, catalysts & solvents 1

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

Procedure

Reaction of 4-trifluoromethylanthranilic acid and methyl 2-iodobenzoate by the reported method [Rewcastle and Denny, Synth, Comm 1987, 17, 309 gave 4-trifluoromethyl-2-(2-methoxycarbonylphenyamino)benzoic acid (43%), mp (MeOH/H2O) 206-207° C. 1H NMR [(CD3)2SO] δ 3.87 (s, 3 H, CO2CH3), 7.12 (ddd, J=8.0, 6.1, 2.1 Hz, 1 H., H-5'), 7.23 (dd, J=8.3, 1.0 Hz, 1 H, ArH), 7.55-7.62 (m, 3 H, 3×ArH), 7.95 (dd, J=8.0, 1.3 Hz, 1 H, ArH), 8.12 (d, J=8.2 Hz, 1 H, ArH). Formation of the corresponding imidazolide and immediate reduction of this as above gave methyl-2-[N-(5'-trifluoromethyl-2'-hydroxymethyl)phenyl-amino]benzoate (86%), mp (hexane) 86-87° C. 1H NMR (CDCl3) δ 2.00 (t, J=5.6 Hz, 1 H, OH), 3.92 (s, 3 H, CO2CH3), 4.78(d, J=5.3 Hz, 2 H, CH2), 6.84 (td, J=7.6, 1.1 Hz, 1 H, ArH), 7.15 (dd, J=8.6, 0.8 Hz, 1 H, ArH), 7.31-7.39 (m, 2 H, 2×ArH), 7.52 (d, J=7.7 Hz, 1 H, ArH), 7.70 (s, 1 H, H-6'), 8.76 (dd, J=8.0, 1.6 Hz, 1 H, ArH), 9.72 (s, 1 H, NH).

Sources & evidence

ORD record
ord-228df72c4a7c4d05917084c3e3cb63f8
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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