Anthranilic Acid → 2-[(2-Methoxy-pyridin-4-ylmethyl)-amino]-benzoic acid

HRID 969675Notes

Reaction equation

HRID 969675 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:11][O:12][C:13]1[CH:18]=[C:17]([CH:19]=O)[CH:16]=[CH:15][N:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[CH:18]=[C:17]([CH2:19][NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])[CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 6101p-Toluenesulfonic acidHCID 27629962-Methoxypyridine-4-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 629894842-[(2-Methoxy-pyridin-4-ylmethyl)-amino]-benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of anthranilic acid (1.37 g, 1.0 mmol), 2-methoxy-pyridine-4-carbaldehyde (1.37 g, 1.0 mmol), and p-toluenesulfonic acid mohohydrate (0.025 g, 0.13 mmol) in 30 mL of anhydrous toluene was stirred at reflux for 1 h, cooled to RT, and NaBH4 (0.9 g) was added. The mixture was stirred at RT for 30 min, and quenched with MeOH. The volatiles were removed under reduced pressure, and the residue was taken up in water. AcOH was added to bring pH to 4, and the mixture was extracted with EtOAc. The combined organic portions were washed with brine, dried over MgSO4, filtered, and condensed. The residue was purified by flash column chromatography to give the titled compound. MS (ES+): 259.0 (M+H)+. Calc'd for C14H12N2O3-258.10.

Workup

  1. temperatureat reflux for 1 h
  2. stirringThe mixture was stirred at RT for 30 min
  3. customquenched with MeOH
  4. customThe volatiles were removed under reduced pressure
  5. additionAcOH was added
  6. extractionthe mixture was extracted with EtOAc
  7. washThe combined organic portions were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customcondensed
  11. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-57dc88a6beba4ba48211edb37dfd0171
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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