Hydrochloric Acid → 2-Chloro-4-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-oxo-4-trifluoromethyl-1,2-dihydro-quinolin-6-yl)-propyl]-phenoxy}-benzonitrile

HRID 2096847Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:42])[C:18]([OH:41])([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[N:29]=[C:28]([O:33]C(C)C)[CH:27]=[C:26]4[C:37]([F:40])([F:39])[F:38])[C:19]([F:22])([F:21])[F:20])=[C:13]([Cl:43])[CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:42])[C:18]([OH:41])([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[NH:29][C:28](=[O:33])[CH:27]=[C:26]4[C:37]([F:38])([F:39])[F:40])[C:19]([F:20])([F:22])[F:21])=[C:13]([Cl:43])[CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To 2-chloro-4-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-2-(2-isopropoxy-4-trifluoromethyl-quinolin-6-yl)-1-methyl-propyl]-phenoxy}-benzonitrile (53 mg) was added acetic acid (270 mg) and aqueous HCl (37%, 92 mg). The mixture was stirred at 60° C. for 24 h. The mixture was neutralized with aqueous NaOH solution and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4), filtered and concentrated to dryness to give the title compound (46 mg) as an orange solid. MS (m/e, ISP neg. ion)=599.1 [M−H+].

Workup

extractionextracted with ethyl acetate
washThe organic phase was washed with water
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-e1ac060878f1479585bf661b2ddb8fc5
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450313B2

Reaction notes

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