Ethyl oxoacetate → 7,8-Difluoroquinoxalin-2(1H)-one

HRID 255319

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH2:9])[C:3]=1[NH2:10].[O:11]=[CH:12][C:13](OCC)=O.FC1C=C2C(=CC=1F)NC(=O)C=N2.FC1C(F)=CC=C2C=1N=CC(=O)N2>>[F:8][C:7]1[C:2]([F:1])=[C:3]2[C:4]([N:9]=[CH:13][C:12](=[O:11])[NH:10]2)=[CH:5][CH:6]=1

Participants

Reactant 4

HCID 70211Ethyl oxoacetate

HCID 27367533,4-Difluorobenzene-1,2-diamine

HCID 63243396,7-Difluoro-1,2-dihydroquinoxalin-2-one

HCID 667753765,6-difluoroquinoxalin-2(1H)-one

Product 1

HCID 667734367,8-Difluoroquinoxalin-2(1H)-oneYield 64.3%

Procedure

3,4-Difluorobenzene-1,2-diamine (4.6 g, 31.6 mmol) and ethyl oxoacetate (50 wt % in toluene, 13.0 mL, 63.2 mmol) were reacted as described for Intermediate 152 to give 3.7 g of product as an off white solid, mixture with 30% of the regioisomer 5,6-difluoroquinoxalin-2(1H)-one. The mixture was carried on to the next step.

Sources & evidence

ORD record: ord-b452eb5bfcf7484e963a655f25c3e386
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875715B2

Linked notes

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