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

HRID 750185Notes

Reaction equation

HRID 750185 reaction equation
[CH2:1]([O:8][N:9]1[C:18]([C:19](O)=[O:20])=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:28])[CH:15]=2)[C:10]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:33])=O>C1COCC1.CN(C=O)C>[CH2:1]([O:8][N:9]1[C:18]([C:19]([Cl:33])=[O:20])=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:28])[CH:15]=2)[C:10]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 230607592-benzyloxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

Product 1

HCID 230607832-Benzyloxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Benzyloxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (240 mg) was dissolved in THF (4.8 ml), and oxalyl chloride (100 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-benzyloxy-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-0eb4e960a93f4099a48c1810ff742d0d
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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