Phenol → HCID 32388, compound

HRID 1940572Notes

Reaction equation

HRID 1940572 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][N:19]=[CH:20]2>N1C=CC=CC=1>[C:1]1([C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][N:19]=[CH:20]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 7364875-Bromoisoquinoline

Product 1

HCID 32388HCID 32388, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

Cupric oxide (0.2 g) was added in one portion to a mixture of phenol (2 g, 21 mmol), potassium carbonate (2.7 g, 20 mmol), and 5-bromoisoquinoline (2.1 g, 10 mmol) in pyridine (20 ml) heated at 90° C. under nitrogen. The mixture was then heated at 140° C. for 18 h. After this time the pyridine was removed in vacuo, the residue suspended in ether and the mixture filtered through a pad of silica gel. The solvent was evaporated and the residue purified by column chromatography on silica with ethyl acetate/hexane (1:3-1:1) as eluant to give the title compound as a colourless solid (1.1 g, 49%); δH (CDCl3) 7.1-7.5 (7H, m, ArH), 7.75 (1H, d, J 8 Hz, ArH), 8.02 (1H, d, J 8 Hz, ArH), 8.57 (1H, d, J 8 Hz, ArH), and 9.3 (1H, s, 1-H).

Workup

  1. temperatureThe mixture was then heated at 140° C. for 18 h
  2. customAfter this time the pyridine was removed in vacuo
  3. filtrationthe mixture filtered through a pad of silica gel
  4. customThe solvent was evaporated
  5. customthe residue purified by column chromatography on silica with ethyl acetate/hexane (1:3-1:1) as eluant

Sources & evidence

ORD record
ord-8461d50f9b4b4bd0a5dc0a77ae38d104
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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