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Oxalyl chloride (18.22 g, 0.144 mol) in dichloromethane (180 ml, dried over molecular sieves) was cooled to -70° C., and a solution of dimethylsulphoxide (13.08 g, 0.168 mol) in dry dichloromethane (20 ml) added dropwise under nitrogen with stirring, keeping the temperature below -60° C. After 30 minutes, a solution of 3-butyryl-4-(2-methylphenylamino)-8-hydroxymethylquinoline (40 g, 0.12 mol) in dry dichloromethane (700 ml) was added dropwise below -60° C. After a further 30 minutes, triethylamine (102 ml) was added dropwise, and the mixture allowed to warm to room temperature, washed with water and dried (Na2SO4). The filtered solution was evaporated to a yellow oil, which crystallised on trituration with ether to give the title compound (33.02 g), m.p. 142°-4°.

1. customthe temperature below -60° C
2. waitAfter a further 30 minutes
3. washwashed with water
4. dry with materialdried (Na2SO4)
5. customThe filtered solution was evaporated to a yellow oil, which
6. customcrystallised on trituration with ether