Methanol → HCID 58345215, compound

HRID 1887988Notes

Reaction equation

[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH3:17]O.[NH2:19][C:20]1[N:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CS(C)=O.ClCCl>[C:14]1([CH3:17])[CH:15]=[CH:16][C:11]([N:10]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[N:1]=[C:22]2[C:21]2[C:20]([NH2:19])=[N:27][CH:26]=[CH:25][CH:24]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-nitro-N-phenylpyridin-2-amine was dissolved in dimethylsulfoxide (4 mL) and methanol (2 mL) in a round bottom flask. 2-aminonicotinaldehyde 4 (77 mg, 1.1 eq.) was added and Na2S2O4 (274 mg). The reaction mixture was heated to 100° C. for 18 hours. After cooling to room temperature the reaction mixture was diluted with dichloromethane (50 mL) and washed with water and brine. The organic phase was separated and dried over Na2SO4. After filtration the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate/hexanes) to afford 20 mg of desired product. 400 M Hz 1H NMR (DMSO-d6) δ: 8.29 (dd, J=1.6 Hz and 5.0 Hz, 1H), 8.17 (dd, J=1.1 Hz and 7.8 Hz, 1H), 7.96 (dd, J=1.6 Hz and 4.7 Hz, 1H), 7.35 (dd, J=5.09 Hz and 8.21 Hz, 1H), 7.31-7.26 (m, 4H), 7.18 (dd, J=1.9 Hz and 7.8 Hz, 1H), 6.96 (s, 2H), 6.37 (dd, J=4.6 Hz and 7.8 Hz, 1H), 2.36 (s, 3H); LCMS [M+H]: 302.

Workup

temperatureAfter cooling to room temperature the reaction mixture
washwashed with water and brine
customThe organic phase was separated
dry with materialdried over Na2SO4
filtrationAfter filtration the solvent
customwas removed under reduced pressure
customThe crude product was purified by silica gel chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-bf6ae1f67c7d4f27a9893198f81daafd
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501770B2

Reaction notes

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