4-Aminobenzoic Acid → HCID 4387480, compound

HRID 1616738Notes

Reaction equation

HRID 1616738 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.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:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:18])([OH:15])=[O:13]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 4387480HCID 4387480, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Aminobenzoic acid (0.50 g, 3.6 mmol) was added to a solution of Meldrum's acid (0.63 g, 4.4 mmol) in toluene (5.0 mL) and treated according to Procedure 1. 4-[(Carboxyacetyl)amino]benzoic acid (0.74 g, 91%) was obtained as a colourless solid; δH (400 MHz, DMSO-d6) 3.38 (br s, 2H, CH2), 7.68 (t, J2,3=J5,6=8.0 Hz, 1H, H2, H6), 7.89 (d, J2,3=J5,6=8.0, 1H, H3, H5), 10.44 (s, 1H, NH), 12.70 (br s, 1H, CO2H).

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-b57b1b3026944fd78e81f3871541bd18
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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