Benzylamine → 2-Benzyl-6-bromo-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

HRID 907276Notes

Reaction equation

HRID 907276 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[CH:6]=[C:5]2[C:13]([O:15][CH3:16])=[O:14].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH2:17]([N:24]1[CH:6]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[C:8]1=[O:12])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 575518316-Bromo-1-oxo-1H-isochromene-4-carboxylic acid, methyl ester

Product 1

HCID 575517152-Benzyl-6-bromo-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the product of Example 37 step ii) (5 g) and benzylamine (3 mL) in methanol (20 mL) was heated at reflux for 40 hours. The reaction was concentrated to half volume, then treated with acetonitrile. The sub-title compound was collected by filtration, washing with acetonitrile (5.30 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 40 hours
  3. concentrationThe reaction was concentrated to half volume
  4. additiontreated with acetonitrile
  5. filtrationThe sub-title compound was collected by filtration
  6. washwashing with acetonitrile (5.30 g)

Sources & evidence

ORD record
ord-91e3ff15f4fc4afe872083d40ef678c3
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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