2,2-Dimethyl-1,3-dioxane-4,6-dione → 2-[(Carboxyacetyl)amino]-5-bromobenzoic acid

HRID 1616741Notes

Reaction equation

HRID 1616741 reaction equation
[Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.CC1(C)O[C:18](=[O:19])[CH2:17][C:15](=[O:16])[O:14]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:18](=[O:19])[CH2:17][C:15]([OH:16])=[O:14])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 798582-Amino-5-bromobenzoic acid

Product 1

HCID 593338562-[(Carboxyacetyl)amino]-5-bromobenzoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Bromoanthranilic acid (0.30 g, 1.4 mmol) was added to a solution of Meldrum's acid (0.24 g, 1.7 mmol) in toluene (5.0 mL) and treated according to Procedure 1. 5-Bromo-2-[(carboxyacetyl)amino]benzoic acid (0.34 mg, 81%) was obtained as a pale brown solid; δH (500 MHz, DMSO-d6) 3.48 (s, 2H, CH2), 7.78 (d, J3,4=8.4 Hz, 1H, H4), 8.04 (s, 1H, H6), 8.40 (d, J3,4=8.4 Hz, 1H, H3), 11.20 (s, 1H, NH), 12.80 (br s, 1H, CO2H); δC (125 MHz, DMSO-d6) 44.7, 114.5, 119.4, 122.5, 133.1, 136.4, 139.4, 164.7, 167.8, 168.9.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-d1ccaefed1e949d286b34df1e750699d
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

Loading…