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

HRID 468685Notes

Reaction equation

HRID 468685 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). 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. Crude 5-bromo-2-[(carboxyacetyl)amino]benzoic acid (0.34 g, 81%) was obtained as a colourless solid; mp 203-206° C.; 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; νmax 1224, 1373, 1520, 1683, 2985 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-b52991f48de34dee86e430e7bd36daf7
Source dataset
uspto-grants-2014_01
Patent number
US08624056B2

Reaction notes

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