2-Isopropylaniline → 3-Butyryl-4-(2-isopropylphenylamino)-8-(2-methylthioethoxy)quinoline

HRID 743105Notes

Reaction equation

[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH:22]([C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27])([CH3:24])[CH3:23]>C(Cl)(Cl)Cl>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:27][C:26]1[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=1[CH:22]([CH3:24])[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 3-butyryl-4-chloro-8-(2-methylthioethoxy)quinoline (400 mg, 1.23 mmol) and 2-isopropylaniline (1.0 g, 7.4 mmol) was heated to 150° C. for 30 min. The mixture was diluted with CHCl3 and extracted with 2N HCl. The organic phase was washed with a saturated sodium bicarbonate solution. The organic layer was dried over Na2SO4 and evaporated. The residue was chromatographed (SiO2 ; CH2Cl2 : MeOH 95:5) yielding 340 mg (80.5%) of the desired product.

Workup

extractionextracted with 2N HCl
washThe organic phase was washed with a saturated sodium bicarbonate solution
dry with materialThe organic layer was dried over Na2SO4
customevaporated
customThe residue was chromatographed (SiO2 ; CH2Cl2 : MeOH 95:5)

Sources & evidence

ORD record: ord-a255f7a0cf674e9e8bac24ce4095ee78
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556863

Reaction notes

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