P(Cl)(Cl)(Cl)=O.CN([CH:9]=[O:10])C.[CH3:11][N:12]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(=O)C.[Na+]>O>[CH3:11][N:12]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH:9]=[O:10])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Phosphorus oxychloride (POCl3, MW 153, 0.06M, 9.18 g) was added dropwise to DMF (MW 73, 0.36M, 26.3 g), maintaining the temperature at <10° C. with external cooling. 1-(N-Methyl-N-phenylamino)-naphthalene (MW 233, 0.06M, 14 g) was added and the reaction stirred at 100° C. for 3 hours. After cooling to room temperature and pouring into water (140 ml) the mixture was neutralised to pH 6 using saturated sodium acetate solution. The aqueous mixture was extracted using dichloromethane (2×50 ml), the combined extracts washed with water (3×100 ml) before drying over MgSO4. The solvent was evaporated under reduced pressure to give 10.4 g of 1-(N-methyl-N-phenylamino)-4-formyl naphthalene as an oil (66% yield).
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