5-Aminosalicylic Acid → N-Acetyl-5-aminosalicylic acid

HRID 2107004Notes

Reaction equation

HRID 2107004 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](OC(=O)C)(=[O:14])[CH3:13]>O>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 7918Acetic Anhydride

Product 1

HCID 65512N-Acetyl-5-aminosalicylic acidYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2-Hydroxy-5-aminobenzoic acid (20.0 g, 0.131 mole) was suspended in water (100 ml), and acetic anhydride (15.0 ml) was added. The reaction mixture was heated to 100° C., with stirring, for 10 minutes, cooled in an ice bath, and the product was isolated by filtration. After recrystallization from water, with activated carbon, analytically pure 2-hydroxy-5-acetamidobenzoic acid (17.0 g, 67%) was obtained, m.p. 218°-220° C. Found (Calc. for C9H9NO4) C 55.10 (55.38), H 4.61 (4.62), N 7.10 (7.18).

Workup

  1. temperaturecooled in an ice bath
  2. customthe product was isolated by filtration
  3. customAfter recrystallization from water

Sources & evidence

ORD record
ord-ef8be6134b0148d396fac84d94b80cf8
Source dataset
uspto-grants-1990_06
Patent number
US04933330

Reaction notes

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