Hydrochloric Acid → HCID 22006213, compound

HRID 323578Notes

Reaction equation

HRID 323578 reaction equation
C[O:2][CH:3](OC)[C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:6]([CH:20](OC)[O:21]C)[N:5]=1.Cl.C(Cl)(Cl)Cl.CO.C([O-])(O)=O.[Na+]>C1COCC1.O>[CH2:13]([O:12][C:10]([C:9]1[C:4]([CH:3]=[O:2])=[N:5][C:6]([CH:20]=[O:21])=[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:8]=1)=[O:11])[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 21584188Chloroform methanolHCID 22006216HCID 22006216, compound

Product 1

HCID 22006213HCID 22006213, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of diethyl 2,6-bis[(dimethoxy)methyl]-3,5-pyridine dicarboxylate (4.40 g, 11.9 mmol) in THF (80 ml) was added 2N HCl (80 ml), and the resulting mixture was heated to 50° C. for 30 minutes. At this time the reaction mixture was treated again with THF (80 ml) and 2N HCl (80 ml). After a total of 1.5 hours, TLC indicated that the reaction was complete (10/1 CHCl3/MeOH). The mixture was cooled and diluted with water (1 L). The pH was 0.94 and was therefore adjusted to 4.5 with solid NaHCO3. The mixture was extracted with EtOAc (2×300 ml) and the combined extracts were dried (MgSO4), filtered and concentrated to afford 1.78 g of crude 3,5-bis(ethoxycarbonyl)-2,6-pyridine dicarboxaldehyde as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 10.42 (s, 2 H), 8.49 (s, 1 H), 4.57 (q, J=7.2 Hz, 4 H), 1.51 (t, J=7.2 Hz, 6 H). 13C NMR (75 MHz, CDCl3) dc 189.83 (s), 164.67 (s), 152.17, 138.75, 130.64, 63.11 (t), 13.90 (q). MS (LR-CI) m/z 280 [M+H]+.

Workup

  1. customAfter a total of 1.5 hours, TLC
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was extracted with EtOAc (2×300 ml)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aa4ef886c2754e959de70ebbf8582216
Source dataset
uspto-grants-2001_04
Patent number
US06214817B1

Reaction notes

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