Cyanoacetamide → 2-Amino-3-quinolinecarboxamide

HRID 1283151Notes

Reaction equation

HRID 1283151 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[O-]CC.[Na+].[NH2:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=O>C(O)C>[NH2:2][C:1]1[C:3]([C:4]([NH2:6])=[O:5])=[CH:14][C:13]2[C:12](=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:11]=1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 682552-AminobenzaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 52002282-Amino-3-quinolinecarboxamideYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Cyanoacetamide (19.4 g., 0.23 mole) is added to a solution of sodium ethoxide (6.65 g., 0.29 mole) in absolute ethanol (460 ml.) maintained at 50° C. The mixture is stirred and o-aminobenzaldehyde (28.0 g., 0.23 mole) in absolute ethanol (100 ml.) added. After fifteen minutes stirring at 50° C., the reaction mixture is cooled in an ice bath, filtered and dried to give 34.5 g. (84% yield) of product; m.p. 240°-242° C.

Workup

  1. stirringAfter fifteen minutes stirring at 50° C.
  2. temperaturethe reaction mixture is cooled in an ice bath
  3. filtrationfiltered
  4. customdried
  5. customto give 34.5 g

Sources & evidence

ORD record
ord-4576fa5033ce484287ab4e9e40821703
Source dataset
uspto-grants-1976_08
Patent number
US03974161

Reaction notes

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