Methanol → HCID 14401276, compound

HRID 1666993Notes

Reaction equation

HRID 1666993 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[O:11][C:12]3[C:17]([N:18]=2)=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:7]=[CH:8][CH:9]=1)([O-])=O.CO.O.[SH-].[Na+]>O>[N:18]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[O:11][C:10]=1[C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14401275HCID 14401275, compoundHCID 16211346Sodium hydrosulfide hydrate

Product 1

HCID 14401276HCID 14401276, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(3-Nitrophenyl)oxazolo[5,4-b]pyridine (600 mg, 2.49 mmol) was mixed with 25 mL of MeOH and 4 mL of water along with 837 mg of sodium hydrosulfide hydrate (14.9 mmol). The reaction mixture was stirred under reflux for 3 hours. It was then cooled to room temperature and concentrated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated to afford 520 mg of 3-(oxazolo[5,4-b]pyridin-2-yl)benzenamine (quantitative crude yield) (MS, M++H=212).

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationconcentrated
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-561012c38eee416299f0fc81881752c2
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

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