1-Naphthoic acid → (2-Methyl-1H-indol-3-yl)(naphthalen-1-yl)methanone

HRID 55931

Reaction equation

HRID 55931 reaction equation
[C:1]1([C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C[Mg+].[Br-].[C:25]1(C(O)=O)C2C(=CC=CC=2)C=CC=1>C(OCC)C.S(Cl)(Cl)=O>[CH3:25][C:14]1[NH:15][C:16]2[C:21]([C:13]=1[C:11]([C:1]1[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=1)=[O:12])=[CH:20][CH:19]=[CH:18][CH:17]=2

Participants

6

Reactant 3

HCID 68471-Naphthoic acidHCID 103558253-NaphthoylindoleHCID 178418689HCID 178418689, compound

Product 1

HCID 11778684(2-Methyl-1H-indol-3-yl)(naphthalen-1-yl)methanoneYield 1,133.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

2-Methylindole 1 (10 g, 76 3 mmol) was dissolved in diethylether (100 ml) under nitrogen atmosphere and cooled to 0° C. MeMgBr (3M) solution (26.7 ml, 80.15 mmol) was added dropwise and allowed to stir at room temperature for 3 hours. In the meantime, 1-naphthoic acid (13.13 g, 76 3 mmol) was dissolved in thionyl chloride (50 ml) and refluxed for 90 min, then the solvent was removed under vacuo and the residue was dissolved in diethylether (50 ml). The resulting solution was added dropwise to the indole reaction mixture at 0° C. and then allowed to stir at room temperature for 2 hours. A solution of ammonium chloride (200 ml) was added to the reaction mixture and the resulting mixture was stirred at room temperature overnight. The solid that was formed was collected by filtration, washed with water and hexane then dried in a dessicator over phosphorous pentoxide to give 9.7 g (45%) (2-methyl-1H-indol-3-yl)(naphthalen-1-yl) methanone 2 as a cream solid.

Workup

  1. temperaturerefluxed for 90 min
  2. customthe solvent was removed under vacuo
  3. dissolutionthe residue was dissolved in diethylether (50 ml)
  4. additionThe resulting solution was added dropwise to the indole reaction mixture at 0° C.
  5. stirringto stir at room temperature for 2 hours
  6. additionA solution of ammonium chloride (200 ml) was added to the reaction mixture
  7. stirringthe resulting mixture was stirred at room temperature overnight
  8. customThe solid that was formed
  9. filtrationwas collected by filtration
  10. washwashed with water and hexane
  11. dry with materialthen dried in a dessicator over phosphorous pentoxide

Sources & evidence

ORD record
ord-ba58fb38ded749dba9c0682a8cc39af9
Source dataset
uspto-grants-2016_09
Patent number
US09434687B2

Linked notes

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