Sodium borohydride → 6-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 899197Notes

Reaction equation

[CH2:1]([C:3]1([CH2:18][CH3:19])[C:8]2[CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=[CH:12][C:7]=2[N:6]([CH3:16])[C:5](=[O:17])[O:4]1)[CH3:2].[BH4-].[Na+]>[Pd].CO>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]2[N:6]([CH3:16])[C:5](=[O:17])[O:4][C:3]([CH2:18][CH3:19])([CH2:1][CH3:2])[C:8]=2[CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of 4,4-diethyl-1-methyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one (3.74 g, 14.15 mmol) and 5% palladium on carbon (0.20 g) in methanol (35 mL) at 0° C. was added sodium borohydride (10.70 g, 28.30 mmol) portionwise. After stirring 1 hr at 0° C., the reaction was quenched with ice and ammonium chloride solution (sat.) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine and dried over magnesium sulfate. Solvent was removed and trituration of the residue with ether gave 6-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one as a yellow solid (2.67 g, 81%). 1H NMR (DMSO-d6): δ 6.78 (d, J=8.6 Hz, 1H), 6.56 (m, 1H), 6.40 (d, J=2.4 Hz, 1H), 4.93 (s, 2H), 3.18 (s, 3H), 1.99 (m, 4H), 0.80 (t, J=7.3 Hz, 6H); MS (ESI) m/z 235 ([M+H]+); Anal. calcd for C13H18N2O2: C, 66.64; H, 7.74; N, 11.96. Found: C, 64.97; H, 7.67; N, 11.62.

Workup

customthe reaction was quenched with ice and ammonium chloride solution (sat.)
extractionextracted with ethyl acetate (3×50 mL)
washThe combined organic layers were washed with brine
dry with materialdried over magnesium sulfate
customSolvent was removed

Sources & evidence

ORD record: ord-c5a2544421c24809bb9b5cf16a6a7f8f
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354915B2

Reaction notes

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