Ethyl 2-(methylamino)benzoate

Yellowish solid; fruity mandarin-type aroma.

Solid|Yellowish solid; Fruity mandarin type aroma

Ethyl N-methylanthranilate is a benzoate ester.

Concentrated sulfuric acid (2 mL, 37 mmol, 98percent) was added to a stirred solution of 2-(methylamino)-benzoic acid 7 (1.1 g, 7.5 mmol) in anhydrous ethanol (16.5 mL). The solution was refluxed for 20 hours, or until the reaction was complete. The solvent was removed under reduced pressure and the residue was re-dissolved in water (20 mL) and neutralised with sodium hydroxide (5 M). The aqueous phase was extracted with chloroform (3 x 20 mL), the organic layers were combined, washed with brine (40 mL), dried over anhydrous magnesium sulfate and the solvent evaporated to yield a brown oil 8 in quantitative yield (1.3 g, 7.5 mmol, 100percent). Rf 0.40 (1/10 v/v ethyl acetate/hexane); IR (ZnSe cell, oil) vmax: 3378 (w, aromatic R2NH), 2981, 2906 (w, C-H), 1677 (s, C=O), 1579, 1517 (m, aromatic C=C), 1233 (s, aromatic R2NH, ester C-O), 1125, 1085 (m, aromatic C=C) cm-1; 1H NMR (300 MHz, d6-DMSO): δ 7.79 (1H, dd, 3J6-5 = 8.1 Hz, 4J6-4 = 1.4 Hz, 6-CH), 7.56 (1H, br, d, 3JNH-10 = 4.2 Hz, NH) 7.40 (1H, ddd, 3J5-6 ~ 3J5-4 = 7.8 Hz, 4J5-3=1.2 Hz, 5-CH), 6.71 (1H, d, 3J3-4 = 8.4 Hz, 3-CH), 6.57 (1H, dd, 3J4-3 ~ 3J4-5 = 7.8 Hz, 4-CH), 4.25 (2H, q, 3J8-9 = 7.02 Hz, 8-CH2-), 2.91 (3H, d, 3J10-NH = 5.1 Hz, 10-CH3), 1.30 (3H, t, 3J9-8 = 7.2 Hz, 9-CH3) ppm; 13C NMR (125 MHz, CDCl3): δ 168.0 (7-C=O), 151.4 (2-C), 133.8 (4-CH), 130.9 (6-CH), 113.6 (5-CH), 110.0 (3-CH), 109.5 (1-C), 59.5 (8-CH2-), 28.8 (10-CH3), 13.7 (9-CH3) ppm; LRMS (+ ESI) m/z: 180 ([M + H]+, 100percent), 162 ([M – C3H5O2 + MeOH + Na + H]+ 56percent), 134 ([M - OCH2CH3]+, 47percent), 130 ([M - (CO2CH2CH3) + Na + H]+, 48percent)

Molecular Weight:179.22
XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:179.094628657
Monoisotopic Mass:179.094628657
Topological Polar Surface Area:38.3
Heavy Atom Count:13
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes