Diethyl squarate → HCID 178467156, compound

HRID 1050984Notes

Reaction equation

HRID 1050984 reaction equation
[NH2:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:9]([O:11][C:12]1[C:13](=O)[C:14](=[O:19])[C:15]=1[O:16]CC)[CH3:10]>C(O)C>[CH2:9]([O:11][C:12]1[C:15](=[O:16])[C:14](=[O:19])[C:13]=1[NH:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1)[CH3:10]

Participants

4

Reactant 2

HCID 123228Diethyl squarateHCID 178418824HCID 178418824, compound

Product 1

HCID 178467156HCID 178467156, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 1.82 g (16.5 mmol, 1 eq) of 3-aminopyridin-2-ol and 3.6 ml (24.8 mmol, 1.5 eq) of 3,4-diethoxycyclobut-3-ene-1,2-dione (3.6 ml, 24.8 mmol) in solution in 87 ml of ethanol was stirred at ambient temperature for 16 hours and then heated at 50° C. for 3 days with formation of a precipitate. Ethanol was added in order to promote the fall of the precipitate, which was filtered off, washed with diethyl ether and dried under vacuum at 45° C. 3.47 g of 3-ethoxy-4-(2-hydroxypyridin-3-ylamino)cyclobut-3-ene-1,2-dione were obtained in the form of a brown solid. Yield=90%.

Workup

  1. temperatureheated at 50° C. for 3 days with formation of a precipitate
  2. filtrationwas filtered off
  3. washwashed with diethyl ether
  4. customdried under vacuum at 45° C

Sources & evidence

ORD record
ord-9651cb5b4365412eb560a7bd277eef5c
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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