HCID 178418361, compound → HCID 178507536, compound

HRID 1747194Notes

Reaction equation

HRID 1747194 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[O:14][C:13]([OH:15])=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[O:14][C:13]([OH:15])=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178526609HCID 178526609, compound

Product 1

HCID 178507536HCID 178507536, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a flask, is dissolved 5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ol (369.90 mg; 1.79 mmol; 1.00 eq.) in MeOH (20.00 ml) under innert atmosphere. Palladium 10% on charcoal (190.03 mg; 0.18 mmol; 0.10 eq.) is added and the reaction mixture is stirred 5 minutes at RT. The mixture is then put under atmospheric pressure of hydrogen. The reaction is completed after 2 hours. The mixture is filtrated on celite and rinced with MeOH. The solvents are evaporated under vacuo, affording 5-(3-aminophenyl)-1,3,4-oxadiazol-2-ol as a white powder (283.30 mg; 89.55%). 1H NMR (DMSO-d6) δ: 5.43 (s, 2H), 6.70 (m, 1H), 6.89 (m, 1H), 7.08 (s, 1H), 7.14 (m, 1H), 12.44 (s, 1H).

Workup

  1. waitThe reaction is completed after 2 hours
  2. filtrationThe mixture is filtrated on celite
  3. customThe solvents are evaporated under vacuo

Sources & evidence

ORD record
ord-0da221d90ee0495faf9de64966bee65d
Source dataset
uspto-grants-2015_10
Patent number
US09150561B2

Reaction notes

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