1,4-Dibromo-2,3-butanedione → 2,3-Bis(bromomethyl)benzo[g]quinoxaline

Reaction equation

[Br:1][CH2:2][C:3](=O)[C:4](=O)[CH2:5][Br:6].[NH2:9][C:10]1[C:19]([NH2:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1>>[Br:1][CH2:2][C:3]1[C:4]([CH2:5][Br:6])=[N:9][C:10]2[CH:11]=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]3=[CH:18][C:19]=2[N:20]=1

Participants

Reactant 2

HCID 227471,4-Dibromo-2,3-butanedione

HCID 698722,3-Diaminonaphthalene

Product 1

HCID 99691272,3-Bis(bromomethyl)benzo[g]quinoxaline

Procedure

Following the procedure of Example 1, 1,4-dibromo-2,3-butanedione is condensed with 2,3-diaminonaphthalene to obtain 2,3-bis(bromomethyl)benzo[g]quinoxaline, m.p. 190°-191° C.; 1H NMR (DMSO-d6, 400 MHz): δ5.07 (s, 4H, CH2), 7.68 and 8.26 (double doublets, 4H, H-7 and H-8, H-6 and H-9, resp.), 8.78 (s, 2H, H-5 and H-10).

Sources & evidence

ORD record: ord-07ff1a7017e741f599a2e607bfbe3dcb
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05118675

Reaction notes

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