Sodium hydride → 5-hydroxy-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one

HRID 604287Notes

Reaction equation

F[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:16])[C:7]2=[O:15].CS(CCO)(=O)=[O:19].[H-].[Na+]>CN(C=O)C>[OH:19][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:16])[C:7]2=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 5-fluoro-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one (2.24 g, 10 mmol) in DMF (15 mL) is added 2-(methylsulfonyl)ethanol (1.86 g, 15 mmol) and the solution cooled to 0° C. Sodium hydride (1.2 g, 30 mmol) is added and the reaction mixture allowed to warm to room temperature and then stirred for 1 hour. The mixture is quenched with a 1N HCl solution and partitioned between ethyl acetate and brine. The organic layer is concentrated to dryness and the crude organics purified by flash column chromatography to give 5-hydroxy-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one in 70% yields. 1H-NMR (400 MHz, δ, ppm) Acetone-d6: 2.85-3.0 (m, 2H), 3.06 (s, 3H), 3.6-3.7 (m, 2H), 7.05-7.1 (m, 1H), 7.35-7.41 (m, 1H), 9.62 (brs, 1H).

Workup

temperatureto warm to room temperature
customThe mixture is quenched with a 1N HCl solution
custompartitioned between ethyl acetate and brine
concentrationThe organic layer is concentrated to dryness
customthe crude organics purified by flash column chromatography

Sources & evidence

ORD record: ord-153055b2a78c4524ae7799508114d5d5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910585B2

Reaction notes

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