Methanol → 8-amino-2-(2-(trifluoromethyl)pyridin-3-yl)-4H-chromen-4-one

HRID 876533Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([C:14]1[C:15]([C:20]([F:23])([F:22])[F:21])=[N:16][CH:17]=[CH:18][CH:19]=1)=[CH:10][C:9]2=[O:24])([O-])=O.[NH4+].[Cl-].CO>[Fe].CCOC(C)=O>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([C:14]1[C:15]([C:20]([F:23])([F:22])[F:21])=[N:16][CH:17]=[CH:18][CH:19]=1)=[CH:10][C:9]2=[O:24]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 8-nitro-2-(2-(trifluoromethyl)pyridin-3-yl)-4H-chromen-4-one 27 (118 mg, 0.38 mmol), Fe (96 mg, 1.7 mmol), sat. aq NH4Cl (7 mL) and MeOH (14 mL) was stirred at 90° C. for 2 h. After cooling to room temperature the reaction mixture was poured into EtOAc and the layers separated. The organic layer was dried (MgSO4) and concentrate to give 28 as a yellow solid (90 mg, 77% yield over two steps).

Workup

temperatureAfter cooling to room temperature the reaction mixture
customthe layers separated
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrate

Sources & evidence

ORD record: ord-871c0ed7a02e45baa1f83c300d4ff084
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987258B2

Reaction notes

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