Phosphorus oxychloride → 2-chloro-N-ethyl-5-nitropyridin-4-amine

HRID 1394225Notes

Reaction equation

HRID 1394225 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][N:7]=[C:6](OC)[CH:5]=1)[CH3:2].O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:6]1[CH:5]=[C:4]([NH:3][CH2:1][CH3:2])[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 45091610N-Ethyl-2-methoxy-5-nitropyridin-4-amine

Product 1

HCID 591770742-chloro-N-ethyl-5-nitropyridin-4-amine

Procedure

A solution of 4-(ethylamino)-2-methoxy-5-nitropyridine (5.0 g, 25.3 mmol) in POCl3 (25 mL) was heated to 100° C. in a sealed tube for 1 week. The reaction mixture was cooled and concentrated and the residue was taken up in EtOAc/H2O and carefully quenched with sat. K2CO3. The aqueous layer was extracted with EtOAc, washed with H2O, dried (MgSO4) and concentrated to give an orange oil which solidified on standing which was used without further purification. MS (ES+) m/e 202 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customcarefully quenched with sat. K2CO3
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washwashed with H2O
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give an orange oil which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-ce55fccfda544220a080323f18148347
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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