Hydrochloric Acid → 6-Cyano-4-(2,3-dimethylindol-5-ylamino)-7-hydroxyquinoline

HRID 2222398Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH3:25])=[C:19]2[CH3:26].Cl>C(O)(C)C>[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[OH:14])[N:5]=[CH:4][CH:3]=[C:2]2[NH:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH3:25])=[C:19]2[CH3:26])#[N:13]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-chloro-6-cyano-7-hydroxyquinoline (852 mg, 4.2 mmol), (prepared as described for the starting material in Example 1), and 5-amino-2,3-dimethylindole (800 mg, 5 mmol) in isopropanol (25 ml) containing 6.2N HCl in isopropanol was heated at 80° C. for 2 hours. After cooling, the solid was collected by filtration, washed with isopropanol followed by ether and dried under vacuum. The solid was partitioned between acetonitrile/ethyl acetate (1/1) and water. The pH of the aqueous layer was adjusted to 7–8 with saturated aqueous sodium hydrogen carbonate followed by 1N citric acid. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated to give 6-cyano-4-(2,3-dimethylindol-5-ylamino)-7-hydroxyquinoline (650 mg, 47%).

Workup

temperatureAfter cooling
filtrationthe solid was collected by filtration
washwashed with isopropanol
customdried under vacuum
customThe solid was partitioned between acetonitrile/ethyl acetate (1/1) and water
customThe organic layer was separated
washwashed with water, brine
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-08314343912e48e7ac6e9a376539de64
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371765B2

Reaction notes

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