Dichloromethane → HCID 178516268, compound

HRID 1482164Notes

Reaction equation

[C:1]([C:3]1[C:9]([C:10]#[N:11])=[C:8]([OH:12])[CH:7]=[CH:6][C:4]=1[OH:5])#[N:2].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[Cl-].[Cl-].[Ca+2].C(Cl)Cl>C(O)CCC.O>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:11]=[C:10]1[C:9]2[C:3](=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=2[OH:12])[C:1](=[N:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[NH:2]1

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of 1.0 g (6.24 mmol) 2,3-dicyanohydroquinone, 1.23 g (13.11 mmol) 2-aminopyridine and 0.14 g (1.3 mmol) CaCl2 in 20 ml 1-butanol was refluxed under N2. Despite the presents of fluorescent blue 2,3-dicyanohydroquinone starting material, as observed by TLC (CH2Cl2), the reaction was discontinued after 20 days. The reaction mixture was poured into 500 mL of H2O. The precipitate was collected by filtration and was washed with water until no blue fluorescents was observed from the filtrate. The precipitate was then dissolved in boiling CH2Cl2 and then cooled to −40° C. overnight. Precipitate was then collected by filtration and washed with MeOH. 0.485 g (24%), yellow needles. MS (Maldi-TOF): m/z=331.85. HRMS-FAB (m/z): [M+H]+ calcd for C18H14N5O2, 332.1142. found, 332.1136. 1H NMR (400 MHz, CDCl3), δ 13.3 (s, 1H), 8.57 (ddd, J=4.8, 2.0, 0.8 Hz, 2H), 7.75 (ddd, J=8.0, 7.6, 2.0 Hz, 2H), 7.35 (d, J=8.0 Hz, 2H), 7.11 (ddd, J=7.6, 4.8, 0.8 Hz, 2H), 7.00 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 159.3, 154.9, 149.0, 147.9, 147.9, 138.1, 122.4, 121.4, 120.4, 116.2.

Workup

filtrationThe precipitate was collected by filtration
washwas washed with water until no blue fluorescents
dissolutionThe precipitate was then dissolved
filtrationPrecipitate was then collected by filtration
washwashed with MeOH

Sources & evidence

ORD record: ord-2933715962d14eb68f1c28b8c7762245
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09412955B2

Reaction notes

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