Hydrochloric Acid → 4-Acetamidosalicylic acid

HRID 2107017

Reaction equation

HRID 2107017 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[Na+].Cl.[C:14](OC(=O)C)(=[O:16])[CH3:15]>O>[OH:1][C:2]1[CH:10]=[C:9]([NH:11][C:14](=[O:16])[CH3:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 2724368Aminosalicylate sodium anhydrous

Product 1

HCID 655094-Acetamidosalicylic acidYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

Sodium 2-hydroxy-4-aminobenzoate (76 g, 0.437 mole) was dissolved in water (2-300 ml) and concentrated hydrochloric acid (36.2 ml) was added after which the precipitated crystalline free acid was isolated by filtration. The acid was suspended in water (700 ml), acetic anhydride (48 ml) was added and the mixture was heated to about 100° C. (supplied with a reflux condenser) for 15 minutes under nitrogen. After cooling, the crystalline material was filtered off and dried in vacuo to give the title compound (48 g, 56%), m.p. 221°-223° C. Found (Calc. for C9H9NO4) C 55.14 (55.38), H 4.73 (4.62), N 7.12 (7.18).

Workup

  1. customwas isolated by filtration
  2. temperatureAfter cooling
  3. filtrationthe crystalline material was filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b629cd53f4a44aa783759b3f39a6ea85
Source dataset
uspto-grants-1990_06
Patent number
US04933330

Linked notes

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