Hydrochloric Acid → 4-Ethyl-4-hydroxy-1H-pyrano[3,4-c]pyridine-3,8(4H,7H)-dione

HRID 30492Notes

Reaction equation

HRID 30492 reaction equation
C(N(CC)[C:4](=[O:18])[C:5]([OH:17])([C:8]1[CH:13]=[CH:12][NH:11][C:10](=[O:14])[C:9]=1[CH2:15][OH:16])[CH2:6][CH3:7])C.C(N(CC)C(=O)C(=O)CC)C.Cl>C(COC)OC>[CH2:6]([C:5]1([OH:17])[C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[C:9]=2[CH2:15][O:16][C:4]1=[O:18])[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10953779N,N-diethyl-2-oxo butyramideHCID 45141716N,N-diethyl-2-hydroxy-2-(3-hydroxymethyl-2-oxo-1,2-dihydro-pyridin-4-yl)-butyramide

Product 1

HCID 101305034-Ethyl-4-hydroxy-1H-pyrano[3,4-c]pyridine-3,8(4H,7H)-dioneYield 21.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 560.0 mg of compound (15) as obtained from example 9 (1.983 mmol) in 11.2 mL dimethoxyethane were added dropwise at 0° C. 1.68 mL concentrated aqueous hydrochloric acid (36.5%) (19.83 mmol, 10.0 eq). The ice bath was removed after 15 min and the triphasic mixture was vigorously stirred. After 4 h, the mixture was evaporated to dryness in a rotary evaporator (27° C., 5 mbar, then 1 mbar). The crude product was obtained as a lightly yellow semisolid (805.4mg, 194% by weight).333.3 mg crude product were purified by trituration with 0.7 mL methanol at room temperature for 18 h furnishing the title compound (168.7 mg, 0.425 mmol, 98% by weight) as white crystals.

Workup

  1. additionwere added dropwise at 0° C
  2. customThe ice bath was removed after 15 min
  3. customthe mixture was evaporated to dryness in a rotary evaporator (27° C., 5 mbar
  4. customThe crude product was obtained as a lightly yellow semisolid (805.4mg, 194% by weight)
  5. custom333.3 mg crude product were purified by trituration with 0.7 mL methanol at room temperature for 18 h

Sources & evidence

ORD record
ord-bc30c2135ffb4ce38ef1aca651f421c6
Source dataset
uspto-grants-2008_09
Patent number
US07423152B2

Reaction notes

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