Ethanol → HCID 22615160, compound

HRID 842640Notes

Reaction equation

HRID 842640 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH:10](N2C(C)=CC=C2C)[CH3:11])[C:5]=1[F:19])[CH3:2].Cl.[NH2:21]O.[OH-].[K+].C(O)C>O>[NH2:21][CH2:11][CH2:10][C:6]1[C:5]([F:19])=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 22615168HCID 22615168, compound

Product 1

HCID 22615160HCID 22615160, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 825 mg (3.15 mmole) of N-[(4-Ethoxy-3-fluoropyrid-2-yl)eth-2-yl]-2,5-dimethylpyrrole, 1.4 g (20.1 mmole) of hydroxylamine hydrochloride, 700 mg (12.5 mmole) of potassium hydroxide, 20 ml of ethanol, and 8 ml of water was refluxed for 3 days under nitrogen. The solution was cooled to room temperature, concentrated, and partitioned between 50 ml of 2N hydrochloric acid and ethyl acetate (3×). The aqueous layer was basified with 5N sodium hydroxide, extracted with ethyl acetate (3×), dried over sodium sulfate, and concentrated. The resulting red oil was found to be the titled compound with a small amount of 2,5-hexanedione dioxime also present. The oil was used as such for reaction without further purification: IR (KBr, cm−1) 2989, 1609, 1495, 1306, 1075; 1H NMR (300 MHz, DMSO-d6) δ 8.18 (d, 11H), 7.05 (t, 1H), 4.20 (q, 2H), 2.60-3.00 (m, 6H), 1.38 (t, 3H); MS (FD) m/e 185 (Mt).

Workup

  1. temperaturewas refluxed for 3 days under nitrogen
  2. concentrationconcentrated
  3. custompartitioned between 50 ml of 2N hydrochloric acid and ethyl acetate (3×)
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customsuch for reaction
  8. customwithout further purification

Sources & evidence

ORD record
ord-327ee7f81bde48deafc7a1dcef6a0be2
Source dataset
uspto-grants-2002_04
Patent number
US06376492B1

Reaction notes

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