Diisopropylethylamine → 6-Bromo-2-(cyclopropylmethyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

HRID 907272Notes

Reaction equation

HRID 907272 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].Cl.[CH:18]1([CH2:21][NH2:22])[CH2:20][CH2:19]1.C(N(CC)C(C)C)(C)C>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:22]([CH2:21][CH:18]1[CH2:20][CH2:19]1)[CH:6]=[C:5]2[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 575518316-Bromo-1-oxo-1H-isochromene-4-carboxylic acid, methyl ester

Product 1

HCID 575517316-Bromo-2-(cyclopropylmethyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the product of step ii) (5.5 g), cyclopropylmethanamine hydrochloride (2.09 g) and N,N-diisopropylethylamine (5.1 mL) in methanol (40 mL) was heated at reflux for 17 hours. The reaction mixture was allowed to cool to room temperature and filtered. The solid was washed with methanol and dried under vacuum at 60° C. to yield the sub-titled compound (4.55 g)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 hours
  3. filtrationfiltered
  4. washThe solid was washed with methanol
  5. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-2989d6a23a884ddd9beff26de69b65f5
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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