Sulfuric Acid → HCID 22649192, compound

HRID 393244Notes

Reaction equation

HRID 393244 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:14])[CH:3]=1.S(=O)(=O)(O)[OH:16]>>[NH2:1][C:2]1[C:11]([C:12](=[O:16])[NH2:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:14])[CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 12486470Methyl 4-amino-5-cyano-2-hydroxybenzoate

Product 1

HCID 22649192HCID 22649192, compound

Conditions

Temperature
80 °C

Procedure

Methyl 4-amino-5-cyano-2-hydroxybenzoate (J. Chem. Soc. Perkin I. 1979, 677; 4 g) was added to stirred concentrated sulphuric acid (6 ml) and the mixture was heated to 80° C. for 30 minutes. The mixture was cooled to ambient temperature and poured onto crushed ice. The resultant solid was filtered off, washed well with water and dried to give methyl 4-amino-5-carbamoyl-2-hydroxybenzoate (2.8 g); NMR Spectrum: (DMSOd6) 3.83 (s, 3H), 6.1 (s, 1H), 6.75 (br m, 2H), 8.08 (s, 1H).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. additionpoured
  3. customonto crushed ice
  4. filtrationThe resultant solid was filtered off
  5. washwashed well with water
  6. customdried

Sources & evidence

ORD record
ord-d5a0c989d63048798b83b9af9e2dfab8
Source dataset
uspto-grants-2004_10
Patent number
US06806274B1

Reaction notes

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