Hydrochloric Acid → 8-(2,4-Dimethylphenyl)-2-methyl-4-(1-propylbutyl)-3,4-dihydro-2H-1,4-benzoxazine

HRID 598068Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[O:17][CH:16]([CH3:19])[C:15](=O)[N:14]([CH:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1.B.O1CCCC1.Cl.[OH-].[NH4+]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[O:17][CH:16]([CH3:19])[CH2:15][N:14]([CH:21]([CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH3:27])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-(2,4-dimethylphenyl)-2-methyl-4-(1-propylbutyl)-2H-1,4-benzoxazin-3(4H)-one (50 mg, 0.14 mmol) was added dropwise to borane-tetrahydrofuran complex (1M solution in tetrahydrofuran, 1.37 ml, 1.4 mmol) in tetrahydrofuran (2 ml) with ice-cooling. The mixture was refluxed for 24 h and then decomposed at room temperature by dropwise addition of 6N hydrochloric acid (2 ml). The mixture was stirred at 50° C. for 30 min. The acidic solution was made alkaline with excess ammonium hydroxide, and the basic mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting with 1% ethyl acetate/n-hexane to afford 15 mg (31%) of the title compound.

Workup

temperaturecooling
temperatureThe mixture was refluxed for 24 h
extractionthe basic mixture was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum
customThe residue was purified by column chromatography
washeluting with 1% ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-daf28040c9764131ac3d9df0b3df6552
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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