1-Naphthalenecarbonyl chloride → HCID 57590938, compound

HRID 1783780Notes

Reaction equation

HRID 1783780 reaction equation
[C:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Al+3].[CH2:18]([C:21]1[N:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]2=[CH:23][N:22]=1)[CH2:19][CH3:20]>ClCCCl>[CH2:18]([C:21]1[N:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]2=[C:23]([C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[O:12])[N:22]=1)[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 701461-Naphthalenecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 39235652HCID 39235652, compound

Product 1

HCID 57590938HCID 57590938, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 1-naphthoyl chloride (409 ml, 2.70 mmol, 2 eq) in 1,2-dichloroethane (10 ml) was added aluminum trichloride (415 mg, 3.11 mmol, 2.3 eq). The reaction mixture was stirred at room temperature for 10 min., then a solution of 3-propyl-imidazo[1,5-a]pyridine (216 mg, 1.35 mmol) in 1,2-dichloroethane (5 ml) was added. The reaction mixture was stirred at room temperature for 1 h. Then washed with saturated aqueous sodium bicarbonate and the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica to yield the title compound (119 mg, 28%). 1H NMR (DMSO-d6) δ 8.59 (1H), 8.28 (1H), 8.10-8.01 (3H), 7.80 (1H), 7.61 (1H), 7.57 (1H), 7.43 (1H), 7.41 (1H), 7.12 (1H), 2.92 (2H), 1.67 (2H), 0.09 (3H); m/z (M+H)=315.17.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. washThen washed with saturated aqueous sodium bicarbonate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-ae8899dc610b4f739c22e27bf6b1eba5
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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