3-Amino-5-nitrobenzoic acid → 3-Nitro-5-(3,6,9-trioxadecanamido)benzoic acid

HRID 437380Notes

Reaction equation

HRID 437380 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:14](Cl)(=[O:24])[CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23]>O1CCOCC1>[N+:11]([C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([NH:1][C:14](=[O:24])[CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH:10]=1)[C:5]([OH:7])=[O:6])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 2393423-Amino-5-nitrobenzoic acidHCID 27595712-[2-(2-Methoxyethoxy)ethoxy]acetyl chloride

Product 1

HCID 706236753-Nitro-5-(3,6,9-trioxadecanamido)benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 14.6 g. of 3-amino-5-nitrobenzoic acid and 17.1 g. of 3,6,9-trioxadecanoic acid chloride in 200 ml. of dioxane was heated at reflux for 24 hours. The reaction mixture was concentrated to remove the solvent. The residue was dissolved in dilute sodium hyroxide and then acidifed with hydrochloric acid. The resulting product (13.6 g., m.p. 130° C.) was recrystallized from acetonitrile to give 3-nitro-5-(3,6,9-trioxadecanamido)benzoic acid as a beige solid, m.p. 136°-137° C.

Workup

  1. additionA mixture of 14.6 g
  2. temperatureat reflux for 24 hours
  3. concentrationThe reaction mixture was concentrated
  4. customto remove the solvent
  5. dissolutionThe residue was dissolved in dilute sodium hyroxide
  6. customThe resulting product (13.6 g., m.p. 130° C.) was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-e57ff0299f1b4efca11fa7ead4f25958
Source dataset
uspto-grants-1977_06
Patent number
US04031088

Reaction notes

Loading…