HCID 58577473, compound → HCID 58577453, compound

HRID 587422Notes

Reaction equation

HRID 587422 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:23]([N+:24]([O-])=O)=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:13][CH:12]=1>CO.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18]2[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 58577473HCID 58577473, compound

Product 1

HCID 58577453HCID 58577453, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(1,3-benzoxazol-2-yl)-N′-(3-nitropyridin-2-yl)benzene-1,4-diamine (0.330 g) in methanol (20 mL) was treated with palladium on carbon (0.060 g, 10% wt on activated carbon) and the mixture was hydrogenated (1 atm H2) for 1 h. After this time, the reaction mixture was filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure to afford N2-[4-(1,3-benzoxazol-2-ylamino)phenyl]pyridine-2,3-diamine (0.294 g) as a yellow solid.

Workup

  1. customfor 1 h
  2. filtrationAfter this time, the reaction mixture was filtered through diatomaceous earth
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f5203957e28d4ba3bf2efcaf02f37b0a
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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