Oxalyl chloride → HCID 23060871, compound

HRID 750220Notes

Reaction equation

HRID 750220 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[C:20]([C:21](O)=[O:22])=[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([Br:30])[CH:17]=4)[C:12]3=[O:31])=[CH:9][C:4]=2[O:3][CH2:2]1.C(Cl)(=O)C([Cl:35])=O>C1COCC1.CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[C:20]([C:21]([Cl:35])=[O:22])=[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([Br:30])[CH:17]=4)[C:12]3=[O:31])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 23060580HCID 23060580, compound

Product 1

HCID 23060871HCID 23060871, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(Benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (200 mg) was dissolved in THF (6.0 ml) and oxalyl chloride (71 μl) and DMF (1 drop) were added at 0° C. with stirring, and 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 and dried to give 2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-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
  4. customdried

Sources & evidence

ORD record
ord-1f8110eeaffe47ef90caeb17b87f8e6e
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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