Ammonia → HCID 15336554, compound

HRID 1078258Notes

Reaction equation

HRID 1078258 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH:8]2[O:10][CH2:11][CH2:12][O:13][CH:7]2[CH2:6][C:5]1=O)[CH:2]=[CH2:3].[C:15]([O:19]C)(=O)[C:16]#[CH:17].[NH3:21]>>[CH2:1]([CH:4]1[C:5]2[NH:21][C:15](=[O:19])[CH:16]=[CH:17][C:6]=2[CH2:7][C:8]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:9]1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 13536Methyl propiolateHCID 67745285HCID 67745285, compound

Product 1

HCID 15336554HCID 15336554, compoundYield 60%

Conditions

Temperature
150 °C

Procedure

A mixture of 2 (1.96 g, 10 mmol), methyl propiolate (1.68 g, 20 mmol), and 40 mL of ammonia-saturated methanol in a 300 mL stainless steel Parr reaction vessel was heated to 150° C. for 6 h. After cooling, the solvent was removed under reduced pressure, and the crude product was purified by flash chromatography with 3% MeOH in CH2Cl2 as the eluent to afford 2.96 g (60%) of the pyridone 3: Rf =0.40 (10% MeOH in CH2Cl2); IR (KBr) 3448, 2887, 1649, 1618, 1093 cm-1 ; 1H NMR δ6.38 (d, 1H, J=9.3 Hz), 5.75 (m, 1H), 5.11 (m, 2H), 3.97 (m, 3H), 3.10 (m, 1H), 2.70 (m, 4H), 1.85 (m, 2H); 13C NMR δ164.7, 143.9, 143.2, 118.1, 118.0, 111.8, 107.4, 64.6, 64.4, 37.6, 36.8, 35.8, 34.8.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure
  3. customthe crude product was purified by flash chromatography with 3% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-5d9dab4563c34c6eb3f255b8b3858690
Source dataset
uspto-grants-1996_08
Patent number
US05547960

Reaction notes

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