Benzoic anhydride → Benzoic Acid

HRID 1366743Notes

Reaction equation

HRID 1366743 reaction equation
[C:1]([O:9]C(=O)C1C=CC=CC=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC1C2C(=CC(O)=CC=2)C=CN=1>N1C=CC=CC=1>[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7167Benzoic anhydrideHCID 1357539911-Aminoisoquinolin-6-ol

Product 1

HCID 243Benzoic AcidYield 108.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
125 °C

Procedure

Benzoic anhydride (10.27 g) was added to a solution of 1-aminoisoquinolin-6-ol (3.312 g) in pyridine (53 ml) at ambient temperature. The mixture was heated at 125° C. for 1 h, the pyridine was removed under reduced pressure and excess pyridine was removed by azeotroping with toluene (X2). Water was added and the mixture extracted with dichloromethane (X3), dried (sodium sulphate) and concentrated in vacuo to give a solid precipitate. Recrystallisation with dichloromethane-diethyl ether gave benzoic acid 1-benzylaminoisoqinolin-6-yl ester (6 g), EIMS: m/z=369.1 [M+H]+.

Workup

  1. customthe pyridine was removed under reduced pressure and excess pyridine
  2. customwas removed
  3. customby azeotroping with toluene (X2)
  4. additionWater was added
  5. extractionthe mixture extracted with dichloromethane (X3)
  6. dry with materialdried (sodium sulphate)
  7. concentrationconcentrated in vacuo
  8. customto give a solid precipitate
  9. customRecrystallisation with dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-56f28a8c260948f4857cf613b6e78759
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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