Hydrochloric Acid → 1,3-Dichloro-7-methoxyisoquinoline

HRID 1627697Notes

Reaction equation

HRID 1627697 reaction equation
O/[N:2]=[C:3]1/[C:4](=O)[C:5]2[C:10]([CH2:11]/1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.P(Cl)(Cl)(Cl)(Cl)[Cl:16].[ClH:21]>O=P(Cl)(Cl)Cl>[Cl:21][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2)[CH:11]=[C:3]([Cl:16])[N:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 6415827HCID 6415827, compound

Product 1

HCID 716915371,3-Dichloro-7-methoxyisoquinolineYield 85%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
30 °C

Procedure

To a suspension of (E)-2-(hydroxyimino)-6-methoxy-2,3-dihydro-1H-inden-1-one (3.60 g, 20.0 mmol) in POCl3 (120 mL), PCl5 (6.50 g, 31.3 mmol) was added at 0° C., then HCl gas was induced until the solution was saturated. The reaction mixture was stirred at 30° C. for 2 hours. The solvent was removed in vacuo and ice water was added to the residue. The precipitate was collected by filtration, washed with water (30 mL), and dried under high vacuum to give the product (4.50 g, yield 85%) as a solid.

Workup

  1. additionwas added at 0° C.
  2. customThe solvent was removed in vacuo and ice water
  3. additionwas added to the residue
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water (30 mL)
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-d44bfc4d61054151a00e2601508769d3
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

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