Triethylamine → 4-ethylamino-6-isopropyl-3-nitro-1H-pyridin-2-one

HRID 1594083Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[NH:5][C:4](=[O:11])[C:3]=1[N+:12]([O-:14])=[O:13].[CH2:15]([NH2:17])[CH3:16].Cl.CCN(CC)CC>CC#N.C(Cl)Cl>[CH2:15]([NH:17][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[NH:5][C:4](=[O:11])[C:3]=1[N+:12]([O-:14])=[O:13])[CH3:16]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 4-chloro-6-isopropyl-3-nitro-1H-pyridin-2-one (Example 28, step 6) (500 mg, 2.31 mmol) in CH3CN at room temperature is added EtNH2.HCl (565 mg, 6.92 mmol) followed by Et3N (1.29 mL, 9.23 mmol). The reaction mixture is then stirred in a sealed tube at 100° C. for 1.5 h. After cooling, the reaction mixture is diluted with CH2Cl2 and washed with H2O (2×25 mL). The aqueous washes are reextracted once with CH2Cl2, and the combined extracts are dried over Na2SO4 and concentrated to provide 4-ethylamino-6-isopropyl-3-nitro-1H-pyridin-2-one as a yellow-orange solid. The material is sufficiently pure to be used without further purification. 1H NMR (DMSO-d6, 400 MHz) δ 11.1 (br, 1H), 8.93 (m, 1H), 5.73 (s, 1H), 3.37 (dq, J=7.4, 6.8 Hz, 2H), 2.67 (sept, J=6.8 Hz, 1H), 1.17 (t, J=7.4 Hz, 3H) 1.15 (d, J=6.8 Hz, 6H) ppm.

Workup

temperatureAfter cooling
washwashed with H2O (2×25 mL)
dry with materialthe combined extracts are dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-e0a0d803f62b43eab1df325442686611
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07300945B2

Reaction notes

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