2-Methyl-2-butene → 2-benzyl-4-(4-carboxyphenyl)-6-chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750247Notes

Reaction equation

HRID 750247 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4].P([O-])(O)(O)=[O:33].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>O.C(O)CCC.C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:33])=[O:22])=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 865995582-benzyl-6-chloro-4-(4-formylphenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

Product 1

HCID 691564702-benzyl-4-(4-carboxyphenyl)-6-chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterYield 34.2%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-benzyl-6-chloro-4-(4-formylphenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (93 mg), sodium dihydrogenphosphate (26 mg), 2-methyl-2-butene (100 μl), THF (2.0 ml), butanol (1.0 ml) and water (2.0 ml) was added sodium chlorite (73 mg) at 0° C. with stirring, and the mixture was stirred for 1 hr. The solvent was removed and the residue was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (33 mg) as a colorless powder.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. customThe solvent was removed
  3. customthe residue was partitioned between 1N hydrochloric acid and ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e50b868c3f1d436b886a8eefdc5dc53a
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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