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Phosphorus oxychloride → 4-Bromo-1,7-dichloroisoquinoline

HRID 1783757
Notes
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Reaction equation

HRID 1783757 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[CH:5]=[N+:4]([O-])[CH:3]=1.P(Cl)(Cl)([Cl:16])=O>C(Cl)(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[C:5]([Cl:16])=[N:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68900861Isoquinoline, 4-bromo-7-chloro-, 2-oxide

Product 1

HCID 575908854-Bromo-1,7-dichloroisoquinoline

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
66 °C

Procedure

4-bromo-7-chloroisoquinoline 2-oxide (3-7) (1.2 g, 4.64 mmol, 1.0 equiv.) was dissolved in anhydrous CHCl3 (20 mL) and treated dropwise with phosphorus oxychloride (0.649 mL, 6.96 mmol, 1.5 equiv.). The reaction mixture was refluxed at 66° C. LCMS after 3 hours showed only product. The reaction mixture was diluted with ethyl acetate, washed with saturated NaHCO3, and the organic layer was dried over Na2SO4, filtered and concentrated. The residue was triturated with hexane, and filtered to afford the product 3-8. LRMS m/z (M+H) 277.9 found, 277.9 required.

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated with hexane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-1bd7798b5bd140359c3971cf33485571
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07501435B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes