Anthranilic Acid → 2-(2-Carboxyacetamido)benzoic acid

HRID 1616725Notes

Reaction equation

HRID 1616725 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].CC1(C)O[C:17](=[O:18])[CH2:16][C:14](=[O:15])[O:13]1>C1(C)C=CC=CC=1>[C:14]([CH2:16][C:17]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])=[O:18])([OH:15])=[O:13]

Participants

4

Reactant 2

HCID 227Anthranilic AcidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 4399222-(2-Carboxyacetamido)benzoic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Anthranilic acid (181 g, 1.32 mol) and Meldrum's acid (200 g, 1.39 mol) in toluene (1.50 L) were treated according to Procedure 1. 2-[(Carboxyacetyl)amino]benzoic acid (263 g, 89%) was obtained as a colourless solid; mp 171-173° C., lit. [21] 178-180° C.; δH (500 MHz, DMSO-d6) 3.45 (br s, 2H, CH2), 7.16 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.59 (td, J4,5=J5,6=8.0, J3,5=1.5 Hz, 1H, H5), 7.97 (dd, J3,4=8.0, J3,5=1.5 Hz, 1H, H3), 8.44 (d, J5,6=8.0 Hz, 1H, H6), 11.27 (s, 1H, NH), 12.83 (br s, 1H, CO2H), 13.57 (br s, 1H, CO2H); δC (125 MHz, DMSO-d6) 45.0, 117.0, 120.3, 123.1, 131.2, 134.1, 140.4, 164.9, 169.1, 169.3.

Sources & evidence

ORD record
ord-96ba72e48e8f4d6890a039af051ec0df
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

Loading…