Hydrochloric Acid → 2-Aminoterephthalic acid

HRID 258060

Reaction equation

HRID 258060 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].Cl>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[OH-].[Na+]>[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 79336Dimethyl aminoterephthalate

Product 1

HCID 27248222-Aminoterephthalic acidYield 89%

Reagents, catalysts & solvents 2

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

A representative preparation was done as follows: Dimethyl aminoterephthalate (5 g), cetyltrimethyl ammonium bromide catalyst (0.05 g) and aqueous NaOH solution (5%, 300 ml) were taken in a 500 ml round bottom flask, and heated to and held at about 60° C. for about 2 hours. The mixture was then cooled to about 15°-20° C., and acidified with concentrated HCl when the acid of Formula 3 separated as yellow crystals. This was filtered, washed with ice cold water, and dried (yield: 89%).

Workup

  1. customA representative preparation
  2. temperatureheated to and
  3. temperatureThe mixture was then cooled to about 15°-20° C.
  4. customseparated as yellow crystals
  5. filtrationThis was filtered
  6. washwashed with ice cold water
  7. customdried (yield: 89%)

Sources & evidence

ORD record
ord-a8157de3536c4b3ab4ef96abe13fc8c2
Source dataset
uspto-grants-1993_11
Patent number
US05264539

Linked notes

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