Triethylamine → 4-(3-Chloro-2-pyridinyl)aniline

HRID 1822936Notes

Reaction equation

HRID 1822936 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH:16]=[CH:15][C:11](C(O)=O)=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C([N:19](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([C:8]2[CH:16]=[CH:15][C:11]([NH2:19])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Product 1

HCID 221704504-(3-Chloro-2-pyridinyl)aniline

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

The product from Example 24A (104 mg, 0.444 mmol) and triethylamine (0.095 mL, 0.68 mmol) were combined in DMF (3 mL) and treated with diphenylphosphoryl azide (0.14 mL, 0.65 mmol). After stirring for 4 hours, the mixture was treated with water (0.30 mL) and heated at 65° C. for 1 hour. The mixture was allowed to cool to room temperature, diluted with water (7 mL), and extracted with diethyl ether (7 mL). The organic layer was washed with brine (7 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (50% ethyl acetate in hexanes) to provide the title compound.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether (7 mL)
  3. washThe organic layer was washed with brine (7 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ca95ab7ac94d4548a7007a36cb593fce
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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