Methanol → HCID 67305477, compound

HRID 1914004Notes

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.CO.[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:11]1([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:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-Nitro-N-phenylpyridin-2-amine (structure 3 as shown in Scheme 1) was dissolved in dimethylsulfoxide (8 mL/mmol) and methanol (1.5 mL/mmol) in a round bottom flask. 2-aminonicotinaldehyde 4 (1.1 eq.) and Na2S2O4 (85%, 2.5 eq.) were added. The reaction mixture was heated at 100° C. for 15 to 36 hours. After cooling to room temperature the reaction mixture was diluted with dichloromethane (20 mL/mmol) 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 (dichloromethane/methanol; 0-20% methanol over 60 min) to give a yellow to brown solid.

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 (dichloromethane/methanol; 0-20% methanol over 60 min)
customto give a yellow to brown solid

Sources & evidence

ORD record: ord-e32de41890dc4926b10f30e962da674f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609688B2

Reaction notes

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