Dichloromethane → 2-Methyl-4-chloro-8-(2,4,6-trimethylphenyl)-quinoline

HRID 1700116Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[C:5](Br)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1B(O)O.C(Cl)Cl>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[C:5]([C:16]3[C:17]([CH3:22])=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=3[CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Part B: In a mixture of 270 ml dimethoxyethane and 45 ml water, after bubbling through nitrogen gas for 30 minutes, a quantity of 5.0 g ( 19.5 mmol) of 2-methyl-4-chloro-8-bromo-quinoline, 3.5 g (21 mmol) of 2,4,6-trimethyl phenylboronic acid, 13.2 g (42 mmol) Ba(OH)2.8H2O and 0.69 g (0.6 mmol) tetrakis(triphenylphosphine)palladium were subsequently dissolved. After heating to 80° C. for 16 hours and subsequent cooling, 250 ml of water and 500 ml of CH2Cl2 were added. After separation the organic layer was dried over sodium sulphate and concentrated in vacuo. The product was purified on a silicagel column using dichloromethane as eluent. A total of 5.1 g of 2-methyl-4-chloro-8-(2,4,6-trimethylphenyl)-quinoline was obtained (88% yield).

Workup

customafter bubbling through nitrogen gas for 30 minutes
customAfter separation the organic layer
dry with materialwas dried over sodium sulphate
concentrationconcentrated in vacuo
customThe product was purified on a silicagel column

Sources & evidence

ORD record: ord-a7fcd8c715fd4e49bef4d0b8ee54a655
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350750B1

Reaction notes

Loading…