Methanol → 3-(5-Methyl-oxazolo[4,5-b]pyridin-2-yl)-phenylamine

HRID 1667038Notes

Reaction equation

HRID 1667038 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=3)[O:10][C:5]2=[CH:4][CH:3]=1.CO.O.[SH-].[Na+]>O>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:11]3[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=3)[O:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 16211346Sodium hydrosulfide hydrateHCID 596799065-Methyl-2-(3-nitro-phenyl)-oxazolo[4,5-b]pyridine

Product 1

HCID 596798783-(5-Methyl-oxazolo[4,5-b]pyridin-2-yl)-phenylamineYield 45.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Methyl-2-(3-nitro-phenyl)-oxazolo[4,5-b]pyridine (50 mg, 0.196 mmol) was mixed with 6 mL of MeOH along with 2 mL of water and 66 mg of sodium hydrosulfide hydrate. The reaction mixture was stirred under reflux for 2 hours. It was then concentrated and extracted with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated to afford 20 mg of 3-(5-methyl-oxazolo[4,5-b]pyridin-2-yl)-phenylamine.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationIt was then concentrated
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c6955097864344c591f5b57e67291442
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

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