3-Nitrophenylboronic Acid → 6-(3-Nitro-phenyl)4-methyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 844130Notes

Reaction equation

HRID 844130 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][N:5]2[CH3:13].[N+:14]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15]>>[N+:14]([C:17]1[CH:22]=[C:21]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH2:6][N:5]3[CH3:13])[CH:20]=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 226677406-Bromo-3,4-dihydro-4-methyl-2(1H)-quinoxalinone

Product 1

HCID 226677336-(3-Nitro-phenyl)4-methyl-3,4-dihydro-1H-quinoxalin-2-one

Procedure

Prepared according to the procedure for Example 5 from 6-bromo-4-methyl-3,4-dihydro-1H-quinoxalin-2-one (4.8 g, 20 mmol), and 3-nitrophenylboronic acid (4.8 g, 30 mmol). A red powder (0.95 g, 16%): mp 237-243° C. 1H-NMR (DMSO-d6) δ2.88 (s, 3H), 6.9 (d, J=7.9 Hz, 1H), 7.01 (d, J=2 Hz, 1H), 7.11 (dd, J=7.9, 2.0 Hz, 1H), 7.7 (t, J=7.9 Hz, 1H), 8.1 (m, 2H), 8.37 (t, J=0.7 Hz), MS (ESI) m/z 283 (M)+

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-10ac3dcd9183437eb3f9bb3c70798012
Source dataset
uspto-grants-2002_04
Patent number
US06380235B1

Reaction notes

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