Hydroxyamine hydrochloride → 3-Cyano-2-hydroxy-5-methylbenzoic acid

HRID 614828Notes

Reaction equation

HRID 614828 reaction equation
[CH:1]([C:3]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]=1[OH:13])=O.Cl.[NH2:15]O>CN(C)C=O>[C:1]([C:3]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]=1[OH:13])#[N:15]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 130269313-Formyl-2-hydroxy-5-methylbenzoic acid

Product 1

HCID 130269333-Cyano-2-hydroxy-5-methylbenzoic acidYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Formyl-5-methylsalicylic acid (3.6 g) was dissolved in dimethylformamide (20 ml) and treated with hydroxylamine hydrochloride (1.53 g). The mixture was heated at reflux for 10 minutes and then the solvent was removed in vacuo. The residue was treated with water (20 ml) and hydrochloric acid (2N; 10 ml). The precipitated solid was filtered off and recrystallized from aqueous ethanol to give 3-cyano-5-methylsalicylic acid (2.7 g), m.p. 193°-194° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 minutes
  3. customthe solvent was removed in vacuo
  4. additionThe residue was treated with water (20 ml) and hydrochloric acid (2N; 10 ml)
  5. filtrationThe precipitated solid was filtered off
  6. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-6bf09be2664f41b7aeee29e79df865ca
Source dataset
uspto-grants-1979_03
Patent number
US04146631

Reaction notes

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