Benzoic acid, 2-iodo-, methyl ester → Benzoic Acid

HRID 1952885Notes

Reaction equation

HRID 1952885 reaction equation
N[C:2]1[C:10](C(F)(F)F)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].COC(=O)C1C=CC=CC=1I>CO.O>[C:4]([OH:6])(=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1

Participants

4

Reactant 2

HCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 6045692-Amino-3-(trifluoromethyl)benzoic acid

Product 1

HCID 243Benzoic AcidYield 51%

Reagents, catalysts & solvents 1

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

Procedure

Similar reaction of 2-amino-3-trifluoromethylbenzoic acid and methyl-2-iodobenzoate by the reported method [Rewcastle and Denny, Synth. Comm, 1987, 17, 309] gave 3-trifluoromethyl-2-[(2-methoxycarbonyl)phenyl)amino]benzoic acid (51%), mp (MeOH/H2O) 113-115° C. 1H NMR [(CD3)2SO] δ 3.89 (s, 3 H, CO2CH3), 6.35 (d, J=8.5 Hz, 1 H, ArH), 6.78 (t, J=7.5 Hz, 1 H, ArH), 7.30 (ddd, J=7.8, 7.8, 1.6 Hz, 1 H, ArH), 7.59 (t, J=7.8 Hz, 1 H, ArH), 7.88 (dd, J=8.0, 1.5 Hz, 1 H, ArH), 8.03 (d, J=7.4 Hz, 1 H, ArH), 8.07 (d, J=8.07 Hz, 1 H, ArH), 9.49 (s, 1 H, NH), 13.15 (br s, 1 H, COOH). Anal. (C16H12F3NO2) C, H, N, F.

Sources & evidence

ORD record
ord-40b6b505c68a423a9494f74240358d78
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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