Oxalyl chloride → 2-Butoxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonyl chloride

HRID 750182Notes

Reaction equation

HRID 750182 reaction equation
[CH2:1]([O:5][N:6]1[C:15]([C:16](O)=[O:17])=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:25])[CH:12]=2)[C:7]1=[O:26])[CH2:2][CH2:3][CH3:4].C(Cl)(=O)C([Cl:30])=O>C1COCC1.CN(C=O)C>[CH2:1]([O:5][N:6]1[C:15]([C:16]([Cl:30])=[O:17])=[C:14]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:25])[CH:12]=2)[C:7]1=[O:26])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 230609102-Butoxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid

Product 1

HCID 230606672-Butoxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Butoxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (370 mg) was dissolved in THF(6.0 ml), and oxalyl chloride (170 μl) and DMF (1 drop) were added at 0° C. with stirring. The mixture was stirred at room temperature for 2 hrs. and concentrated under reduced pressure. Toluene was added to the residue and they were boiled together several times to give 2-butoxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonyl chloride.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hrs
  2. concentrationand concentrated under reduced pressure
  3. additionToluene was added to the residue and they

Sources & evidence

ORD record
ord-15fdaf0cd275498d83014c3184926315
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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