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

HRID 1763288Notes

Reaction equation

HRID 1763288 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 hydroxide and then acidified 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 hydroxide
  6. customThe resulting product (13.6 g., m.p. 130° C.) was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-dc2c5a617c5446d0861d186211b5af33
Source dataset
uspto-grants-1978_09
Patent number
US04111937

Reaction notes

Loading…