Hydrochloric Acid → HCID 22226942, compound

HRID 1745918Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[C:16]3[CH:17]=[CH:18][C:19]([O:21]C)=[CH:20][C:15]=3[N:14]=[CH:13]1)[CH:8]=[CH:7]2.[OH-].[Na+].Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[C:16]3[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:15]=3[N:14]=[CH:13]1)[CH:8]=[CH:7]2

Participants

Conditions

Temperature: -78 °C

Procedure

To a pre-cooled (−78° C.) solution containing 8-chloro-2-(5-methoxy-1H-benzimidazol-1-yl)quinoline 138B (2.16 g, 7.0 mMol) in anhydrous DCM (28 mL) was added a 1.0 M solution of borontribromide in DCM (20.9 mL, 20.9 mMol). The cooling bath was removed and the reaction mixture stirred at ambient temperature under nitrogen for 22 hours. The reaction was quenched by the addition of aqueous 1 N NaOH to a pH of about 8.8. After stirring for about minutes, the suspended solids were removed by filtration. The solids were subsequently stirred briefly with 1 N NaOH (21 mL, 21 mMol) to hydrolyse remaining borate esters, and then neutralized by adding 1 N HCl (21 mL, 21 mMol). The solid precipitate was filtered off, stirred briefly with a small amount of warm EtOAc to remove traces of starting material, and re-filtered to give 1.91 g, mp>250° C., of the title product 138C.

Workup

customThe cooling bath was removed
customThe reaction was quenched by the addition of aqueous 1 N NaOH to a pH of about 8.8
stirringAfter stirring for about minutes
customthe suspended solids were removed by filtration
filtrationThe solid precipitate was filtered off
stirringstirred briefly with a small amount of warm EtOAc
customto remove traces of starting material
filtrationre-filtered
customto give 1.91 g, mp>250° C.

Sources & evidence

ORD record: ord-5ac3c3117b1b467591a2305d54f7622f
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07019147B1

Reaction notes

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