Dimethyl Sulfoxide → 3-Butyryl-4-(o-tolylamino)quinoline-8-carbaldehyde

HRID 1647446Notes

Reaction equation

HRID 1647446 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:25]=1[NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33])=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:34][OH:35])(=[O:15])[CH2:12][CH2:13][CH3:14].C(N(CC)CC)C>ClCCl>[C:11]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:25]=1[NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33])=[CH:23][CH:22]=[CH:21][C:20]=2[CH:34]=[O:35])(=[O:15])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 104270103-Butyryl-4-(2-methylphenylamino)-8-hydroxymethylquinoline

Product 1

HCID 103821023-Butyryl-4-(o-tolylamino)quinoline-8-carbaldehydeYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-eb183d01d66e4a6ebd1b5c5aff64f2ae
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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