N-(5-Bromo-4-methoxy-2-nitrophenyl)acetamide → HCID 541150, compound

HRID 2406417Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[O-:6].[K+].Br[C:14]1[CH:19]=[C:18]([NH:20][C:21]([CH3:23])=[O:22])[C:17]([N+:24]([O-:26])=[O:25])=[CH:16][C:15]=1[O:27][CH3:28]>CN(C=O)C.O>[NH:20]([C:18]1[C:17]([N+:24]([O-:26])=[O:25])=[CH:16][C:15]([O:27][CH3:28])=[C:14]([O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[CH:19]=1)[C:21]([CH3:23])=[O:22]

Participants

Conditions

Temperature: 120 °C

Procedure

To the above solid 7 under argon, was added a solution of 3.0 g (10.4 mmol) of bromide 6 in 20 mL of DMF via cannula. The resulting solution was stirred at 120° C. for 1 day. TLC and NMR indicated the presence of a small amount of starting material 6. The reaction solution was cooled to room temperature and 2 mmol of compound 7 was added. The solution was stirred at 120° C. for 12 hour, diluted with 200 mL of ice and water, and the solid was collected by filtration, washed with water, dried under vacuum, and crystallized from ethanol to give 3.04 g (79% yield) of compound 8. 1H NMR (CDCl3) δ 10.4 (s, 1 H, NH), 8.39 (s, 1 H), 7.83 (s, 1 H), 7.5 (m, 2 H), 7.3 (m, 2 H), 3.93 (s, 3 H, OMe), 2.23 (s, 3 H, CH3). 13C NMR (CDCl3) δ 174, 155.7, 153.9, 142.4, 141.6, 130.9, 123.0, 121.7, 121.6, (116.9, 116.8, 116.7, 116.6 q for CF3), 108.7, 106.6, 56.7, 21.8.

Workup

temperatureThe reaction solution was cooled to room temperature
stirringThe solution was stirred at 120° C. for 12 hour
filtrationthe solid was collected by filtration
washwashed with water
customdried under vacuum
customcrystallized from ethanol

Sources & evidence

ORD record: ord-f9490ddca1b440c9a1e1ed83a2f9cae1
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809368B2

Reaction notes

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