Pyridine → HCID 87342601, compound

HRID 1423100Notes

Reaction equation

HRID 1423100 reaction equation
[OH:1][NH:2][C:3](=[NH:5])[CH3:4].N1[CH:11]=[CH:10]C=CC=1.C([CH:14]([C:18](Cl)=[O:19])[C:15](Cl)=[O:16])C.C[O:22]CCOC>>[NH2:5]/[C:3](=[N:2]\[O:1][C:18](=[O:19])[CH2:14][C:15]([O:16][CH2:10][CH3:11])=[O:22])/[CH3:4]

Participants

5

Reactant 4

HCID 1049PyridineHCID 80711,2-DimethoxyethaneHCID 109209242-Ethylpropanedioyl dichlorideHCID 178465666HCID 178465666, compound

Product 1

HCID 87342601HCID 87342601, compoundYield 21%

Conditions

Temperature
0 °C

Procedure

A suspension of N-hydroxyacetamidine (37 g, 0.50 mol) in DME (500 mL) was treated dropwise with pyridine (118.5 g, 1.50 mol) at room temperature under N2 gas atmosphere. The mixture was then cooled to 0° C. and ethyl malonyl chloride (113 g, 0.75 mol) added drop-wise. After stirring at 0° C. for 30 min, then the mixture was warmed to room temperature, quenched with water, separated, the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried, concentrated to dryness. The intermediate was purified by the flash chromatography on silica gel to afford ethyl 3-({[(1Z)-1-aminoethylidene]amino}oxy)-3-oxopropanoate as a colorless solid (20 g, 21%). 1H NMR (CDCl3) 5.00 (br s, 2H), 4.23 (q, J=7.2, 2H), 3.52 (s, 2H), 2.01 (s, 3H), 1.31 (t, J=7.2, 3H).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. customquenched with water
  3. customseparated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. customdried
  7. concentrationconcentrated to dryness
  8. customThe intermediate was purified by the flash chromatography on silica gel

Sources & evidence

ORD record
ord-ec0ca41c16364e2c812320f429a2683c
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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