Hydrochloric Acid → HCID 58764006, compound

HRID 2387101Notes

Reaction equation

HRID 2387101 reaction equation
C([O:3][CH:4](OCC)[C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:6]=1)C.Cl.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:10][N:9]1[C:5]([CH:4]=[O:3])=[N:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:8]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 58764290HCID 58764290, compound

Product 1

HCID 58764006HCID 58764006, compoundYield 45.5%

Conditions

Temperature
45 °C

Procedure

The acetal from step 2, 2-[5-(diethoxymethyl)-1-methyl-1H-1,2,4-triazol-3-yl]pyridine (11.06 g, 0.042 mol) was dissolved in 1.5 equiv of 2 N HCl (aq) and stirred at 40-50° C., overnight. The mixture was concentrated, yielding a viscous oil, which was then basified to pH 10 using saturated aqueous Na2CO3. The mixture was then extracted using ethyl acetate (4×200 mL), the organic layer dried over Na2SO4, filtered and concentrated, to a yellow solid. The solid was dissolved in a minimal amount of hot ethyl acetate, scratched and diluted with hexanes to recrystallize the product, affording 3.6 g (45%) of the desired aldehyde as a yellow powder. 1H NMR (300 MHz, CDCl3): δ 4.28 (s, 3H), 7.46 (m, 1H), 7.82 (m, 1H), 8.15 (m, 1H), 8.78 (m, 1H), 10.08 (s, 1H). MS (APCI) calcd for C9H8N4O: 188.07, found (M+H+): 189.3.

Workup

  1. concentrationThe mixture was concentrated
  2. customyielding a viscous oil, which
  3. extractionThe mixture was then extracted
  4. dry with materialthe organic layer dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated, to a yellow solid
  7. dissolutionThe solid was dissolved in a minimal amount of hot ethyl acetate
  8. additiondiluted with hexanes
  9. customto recrystallize the product

Sources & evidence

ORD record
ord-6251a47941484502a589b28dea62cb88
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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