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72016-31-0

Basic Information
CAS No.: 72016-31-0
Name: Orellanine II
Article Data: 6
Molecular Structure:
Molecular Structure of 72016-31-0 (Orellanine II)
Formula: C10H8N2O4
Molecular Weight: 220.185
Synonyms: (2,2'-Bipyridine)-3,3',4,4'-tetrol;3,3'-dihydroxy-1H,1'H-[2,2']bipyridinyl-4,4'-dione;
Density: 1.684g/cm3
Boiling Point: 257.4°Cat760mmHg
Flash Point: 109.5°C
PSA: 106.18000
LogP: 0.14140
Synthetic route
101664-55-5

3,3',4,4'-tetramethoxy-2,2'-bipyridine

72016-31-0

orelline

Conditions
ConditionsYield
With hydrogen bromide In acetic acid for 5h; Heating;77%
With hydrogen bromide at 150℃; sealed tube, overnight;60%
With hydrogen bromide at 120℃;60%
119767-30-5

3,3'-Bis<<2-(trimethylsilyl)ethoxy>methoxy>-2,2'-bipyridin-4,4'-diol

72016-31-0

orelline

Conditions
ConditionsYield
With hydrogenchloride In methanol for 1h; Heating;75%
405137-22-6

4,4'-dihydroxy-3,3'-dimethoxy-2,2'-bipyridine

72016-31-0

orelline

Conditions
ConditionsYield
With hydrogen bromide In acetic acid for 5h; Heating;71%
104819-53-6

3,3'-dihyroxy-4,4'-dimethoxy-2,2'-bipyridyl

72016-31-0

orelline

Conditions
ConditionsYield
With hydrogen bromide In acetic acid for 5h; Heating;70%
37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

72016-31-0

orelline

Conditions
ConditionsYield
at 220℃; under 0.01 Torr; sublimation;50%
for 336h; Irradiation;
119767-37-2

3,3'-Dihydroxy-2,2'-bipyridin-4,4'-dicarbaldehyd

72016-31-0

orelline

Conditions
ConditionsYield
With dihydrogen peroxide In potassium hydroxide at 60 - 70℃; for 1h;36%

C22H34Li2N2O4Si2

72016-31-0

orelline

Conditions
ConditionsYield
With bis-trimethylsilanyl peroxide In diethyl ether for 0.5h; Ambient temperature;11%
Multi-step reaction with 3 steps
1: 45 percent / 0.5 h / -20 - -15 °C
2: 75 percent / conc. HCl / H2O / 30 h / Heating
3: 36 percent / 30percent H2O2 / aq. KOH / 1 h / 60 - 70 °C
View Scheme
Multi-step reaction with 2 steps
1: 10 percent / 0.5 h / -5 °C
2: 75 percent / 2N HCl / methanol / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 10 percent / bis(trimethylsilyl)-peroxide / 0.5 h / -5 °C
2: 75 percent / 2N HCl / methanol / 1 h / Heating
View Scheme
40263-57-8

2-iodo-3-hydroxypyridine

72016-31-0

orelline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 70 percent / NaH / dimethylsulfoxide / 15 h / 0 - 20 °C
2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C
2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C
2.3: 78 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C
3.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C
4.1: [Pd(PPh3)4]; CuBr / dioxane / 15 h / Heating
5.1: aq. HCl / diethyl ether / 15 h / 20 °C
6.1: 70 percent / aq. HBr / acetic acid / 5 h / Heating
View Scheme
Multi-step reaction with 6 steps
1.1: 85 percent / MeONa / dimethylformamide / 15 h / 0 - 20 °C
2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C
2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C
2.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C
3.1: 69 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C
4.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C
4.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C
4.3: [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating
5.1: aq. HCl / tetrahydrofuran / 7 h / 50 °C
6.1: 71 percent / aq. HBr / acetic acid / 5 h / Heating
View Scheme
Multi-step reaction with 5 steps
1.1: 85 percent / MeONa / dimethylformamide / 15 h / 0 - 20 °C
2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C
2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C
2.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C
3.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C
4.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C
4.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C
4.3: 59 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating
5.1: 77 percent / aq. HBr / acetic acid / 5 h / Heating
View Scheme
93560-55-5

2-iodo-3-methoxy-pyridine

72016-31-0

orelline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C
1.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C
1.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C
2.1: 69 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C
3.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C
3.3: [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating
4.1: aq. HCl / tetrahydrofuran / 7 h / 50 °C
5.1: 71 percent / aq. HBr / acetic acid / 5 h / Heating
View Scheme
Multi-step reaction with 4 steps
1.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C
1.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C
1.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C
2.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C
3.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C
3.3: 59 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating
4.1: 77 percent / aq. HBr / acetic acid / 5 h / Heating
View Scheme
87905-88-2

2-iodo-3-(methoxymethoxy)pyridine

72016-31-0

orelline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C
1.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C
1.3: 78 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C
2.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C
3.1: [Pd(PPh3)4]; CuBr / dioxane / 15 h / Heating
4.1: aq. HCl / diethyl ether / 15 h / 20 °C
5.1: 70 percent / aq. HBr / acetic acid / 5 h / Heating
View Scheme
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