Sodium borohydride → 4-(3-chloro-phenyl)-6-[(5-chloro-thiophen-2-yl)-hydroxy-methyl]-1-methyl-1H-quinolin-2-one

HRID 1936314Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:20]4[S:21][C:22]([Cl:25])=[CH:23][CH:24]=4)=[O:19])[CH:16]=3)[N:11]([CH3:26])[C:10](=[O:27])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([C:20]4[S:21][C:22]([Cl:25])=[CH:23][CH:24]=4)[OH:19])[CH:16]=3)[N:11]([CH3:26])[C:10](=[O:27])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 4-(3-chloro-phenyl)-6-(5-chloro-thiophene-2-carbonyl)-1-methyl-1H-quinolin-2-one (58 mg, 0.154 mmol) in MeOH (1 ml) was added sodium borohydride as solid (NaBH4, 7 mg, 0.185 mmol) at 0° C. The reaction mixture was stirred at 0° C. for one hour after which time it was partitioned between chloroform and water. The organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to give an off-white solid (49 mg, 78.5% yield).

Workup

customwas partitioned between chloroform and water
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-2e5e2fca62834753af934a3a82d36477
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06388092B2

Reaction notes

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