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

HRID 468683Notes

Reaction equation

HRID 468683 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 86.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Anthranilic acid (300 g, 2.08 mol) was added to a solution of Meldrum's acid (272 g, 1.98 mol) in toluene (2.0 L). The reaction flask was fitted with a Dean-Stark apparatus and the suspension was heated to reflux for 3 h. The suspension was cooled, filtered, washed with toluene and dried. 2-[(Carboxyacetyl)amino]benzoic acid (381 g, 86%) was obtained as a colourless solid; mp 171-173° 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; νmax 760, 1234, 1385, 1544, 1684, 1712, 2653, 2964, 3119 cm−1.

Workup

  1. customThe reaction flask was fitted with a Dean-Stark apparatus
  2. temperaturethe suspension was heated
  3. temperatureto reflux for 3 h
  4. temperatureThe suspension was cooled
  5. filtrationfiltered
  6. washwashed with toluene
  7. customdried

Sources & evidence

ORD record
ord-68879547c9414172bf83d1de931a8eb9
Source dataset
uspto-grants-2014_01
Patent number
US08624056B2

Reaction notes

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