Formaldehyde → 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine

HRID 1782188Notes

Reaction equation

HRID 1782188 reaction equation
[H-].[Na+].[H][H].Cl.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][N:20]=2)[O:16][N:15]=1.[CH2:26]=O.[CH:28]([OH:31])([CH3:30])[CH3:29]>O>[Cl:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[C:8]=1[C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[C:23]([NH:25][CH2:26][O:31][CH:28]([CH3:30])[CH3:29])[CH:22]=[CH:21][N:20]=2)[O:16][N:15]=1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 69053436HCID 69053436, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 575884942-(3-(2,6-dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (120 mg, 2.9 mmol) was added slowly to isopropyl alcohol (15 mL) at 0° C. Once the evolution of hydrogen ceased 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-amine hydrochloride (200 mg, 0.58 mmol) and paraformaldehyde (147 mg, 1.64 mmol) added. The resulting mixture was stirred at room temperature for 5 h and hydrolyzed with ice-cooled water and extracted with ethyl acetate. The organic extracts were washed with water, then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine (269 mg). The product was carried forward without further purification. 1H NMR (CDCl3): 8.38 (d, 1H), 7.44 (m, 1H), 7.35 (m, 1H), 7.00 (s, 1H), 6.70 (m, 1H), 4.80 (d, 2H), 3.90 (m, 1H), 1.22 ppm (d, 6H).

Workup

  1. additionadded
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-67ba2c47208b41cfba83c3a8e0553269
Source dataset
uspto-grants-2009_03
Patent number
US07498353B2

Reaction notes

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