Ethyl oxamate → HCID 135705331, compound

HRID 1283166Notes

Reaction equation

HRID 1283166 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:15](OCC)(=O)[C:16]([NH2:18])=[O:17].C[O-].[Na+]>C(O)CO>[N:1]1[C:2]2=[N:3][C:4]3[C:9]([CH:10]=[C:11]2[C:12](=[O:13])[NH:14][C:15]=1[C:16]([NH2:18])=[O:17])=[CH:8][CH:7]=[CH:6][CH:5]=3

Participants

5

Reactant 3

HCID 69238Ethyl oxamateHCID 52002282-Amino-3-quinolinecarboxamideHCID 10942334Sodium Methoxide

Product 1

HCID 135705331HCID 135705331, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 2-aminoquinoline-3-carboxamide (2.0 g., 1.15 millimoles), ethyl oxamate (2.71 g., 23.1 millimoles), ethylene glycol (10 ml.) and sodium methoxide (10 mg.) is heated at 170° C. for 1 hour. The product is precipitated by slow addition of ice cold methanol (50 ml.) to the hot reaction mixture followed by chilling in an ice bath. It is filtered off, washed with cold methanol and dried in vacuo. Yield = 0.768 g. (28%). M.P. 320° C.

Workup

  1. customThe product is precipitated by slow addition of ice cold methanol (50 ml.) to the hot reaction mixture
  2. temperatureby chilling in an ice bath
  3. filtrationIt is filtered off
  4. washwashed with cold methanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-733935f57c3d4e4d9c8e262773fe2820
Source dataset
uspto-grants-1976_08
Patent number
US03974161

Reaction notes

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