4-Methoxybenzylamine → HCID 23061009, compound

HRID 750203Notes

Reaction equation

HRID 750203 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:29]([CH2:28][C:27]1[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1)[C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 103800926-chloro-4-phenylisocoumarin-3-carboxylic Acid

Product 1

HCID 23061009HCID 23061009, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-chloro-1-oxo-4-phenyl-1H-isochromen-3-carboxylic acid (300 mg), 4-methoxybenzylamine (684 mg) and methanol (3.0 ml) was stirred at room temperature for 12 hrs. The reaction mixture was concentrated, and the residue was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Then, 4N hydrochloric acid ethyl acetate solution (3.0 ml) was added to the residue and the mixture was stirred for 12 hrs. at room temperature. The reaction mixture was concentrated under reduced pressure and dried to give the title compound (360 mg) as a pale-yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between 1N hydrochloric acid and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionThen, 4N hydrochloric acid ethyl acetate solution (3.0 ml) was added to the residue
  6. stirringthe mixture was stirred for 12 hrs
  7. customat room temperature
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customdried

Sources & evidence

ORD record
ord-603a584f04b34bdd953c1f2d6449e3fd
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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