Acetic Acid → HCID 14401275, compound

HRID 416599Notes

Reaction equation

HRID 416599 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](Cl)=[O:16])([O-:11])=[O:10].C(O)(=O)C>N1C=CC=CC=1.CCOC(C)=O>[N+:9]([C:12]1[CH:13]=[C:14]([C:15]2[O:16][C:2]3[C:7]([N:8]=2)=[CH:6][CH:5]=[CH:4][N:3]=3)[CH:18]=[CH:19][CH:20]=1)([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8495Benzoyl chloride, 3-nitro-HCID 805282-Chloro-3-pyridylamine

Product 1

HCID 14401275HCID 14401275, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloropyridin-3-amine (3.20 g, 0.025 mol) was suspended in 15 mL of pyridine and added slowly to a suspension of 3-nitrobenzoyl chloride (4.64 g, 0.025 mol) in 15 mL of pyridine in an ice bath. The reaction mixture was slowly warmed to room temperature and stirred overnight. The next day, the reaction mixture was cooled in an ice bath and 30 mL of glacial acetic acid was added slowly. The resulting mixture was diluted with 200 mL of EtOAc and washed with water (3×20 mL). The organic layer was then dried (Na2SO4) and concentrated. The resulting residue was mixed with 10 mL of PPA and stirred at 160 degree for 6 hours. The reaction mixture was then poured carefully into 150 mL of water. The pH was brought to about 5 with solid NaOH and the solids were collected by filtration and dried. This material was mixed with 50 mL of MeOH and filtered. The filtrate was concentrated to afford 2.1 g of 2-(3-nitrophenyl)oxazolo[5,4-b]pyridine (35% yield) (MS, M++H=242).

Workup

  1. temperatureThe next day, the reaction mixture was cooled in an ice bath
  2. washwashed with water (3×20 mL)
  3. dry with materialThe organic layer was then dried (Na2SO4)
  4. concentrationconcentrated
  5. additionThe resulting residue was mixed with 10 mL of PPA
  6. stirringstirred at 160 degree for 6 hours
  7. additionThe reaction mixture was then poured carefully into 150 mL of water
  8. filtrationthe solids were collected by filtration
  9. customdried
  10. additionThis material was mixed with 50 mL of MeOH
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-242870c7d98546b6be42ba637edc49f9
Source dataset
uspto-grants-2012_01
Patent number
US08088928B2

Reaction notes

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