Hydrochloric Acid → 4-Acetamidonaphthalene-1-sulfonic acid

HRID 1789407

Reaction equation

HRID 1789407 reaction equation
[C:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.Cl>O>[C:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([S:15]([OH:18])(=[O:16])=[O:17])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13306497pyridine N-acetyl-1-aminonaphthalene-4-sulphonate

Product 1

HCID 4169954-Acetamidonaphthalene-1-sulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15 g (0.04 mole) of pyridine N-acetyl-1-aminonaphthalene-4-sulphonate is dissolved in the minimum amount of water in an Erlenmeyer flask. This solution is conveniently cooled and is acidified with concentrated hydrochloric acid, following which the precipitate formed is collected in a filter to give N-acetyl-1-amino-4-naphthalenesulphonic acid, which is then filtered, washed and dried, and suspended in water. An aqueous solution of the stoichiometric amount of tranexamic acid (AMCHA) is then added, and the mixture is stirred for 15 minutes at ambient temperature and evaporated to dryness. The residue obtained is recrystallized in absolute alcohol, 14.1 g (Yield 76.6%) of AMCHA N-acetyl-1-aminonaphthalene-4-sulphonate finally being obtained, whose m.p. is 214°-215° C. and whose IR spectrum (KBr) has the following bands: 1,670; 1,650; 1,530; 1,510; 1,370; 1,320; 1,200; 1,040; 750; 670; 640.

Workup

  1. temperatureThis solution is conveniently cooled
  2. customformed
  3. customis collected in
  4. filtrationa filter

Sources & evidence

ORD record
ord-c6d541891e04442aabb122c5d2326b45
Source dataset
uspto-grants-1987_08
Patent number
US04689346

Linked notes

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