Aluminum(III) Chloride → HCID 135848746, compound

HRID 1374676Notes

Reaction equation

HRID 1374676 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[N:8][CH:7]=[C:6]2[Cl:13].[Cl-].[Cl-].[Cl-].[Al+3]>C1(C)C=CC=CC=1>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[N:8][CH:7]=[C:6]2[Cl:13]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 21077807HCID 21077807, compound

Product 1

HCID 135848746HCID 135848746, compoundYield 121.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 6-methoxy-4-chlorocinnoline (135 mg, 0.7 mmol) in toluene (7 ml) was added to a stirred suspension of aluminium trichloride (231 mg, 1.73 mmol) in toluene (7 ml) and the red brown suspension was refluxed for 1 hr. The solvent was removed under vacuum and the residue was partitioned between water (20 ml) and 10% ethanol/chloroform (2×100 ml). The organic layer was washed with brine and dried (Na2SO4). Removal of the solvent under vacuum gave 6-hydroxy-4-chlorocinnoline (154 mg) as a single component by TLC (1:1 ethylacetate/hexanes). δH (CD3OD)=7.33 (d, 1H); 7.56 (dd, 1H); 8.32 (d, 1H) and 9.15 (br s 1H). MS (ESI) (M+H)+ 181.

Workup

  1. temperaturethe red brown suspension was refluxed for 1 hr
  2. customThe solvent was removed under vacuum
  3. customthe residue was partitioned between water (20 ml) and 10% ethanol/chloroform (2×100 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-b893b55c76724f509d363e95bfbf2c47
Source dataset
uspto-grants-2007_01
Patent number
US07166604B2

Reaction notes

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