Hydrochloric Acid → 2-Amino-4-oxo-4H-1-benzopyran-3-carbonitrile

HRID 1580183Notes

Reaction equation

HRID 1580183 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[OH-].[Na+].C([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15])(=O)C.[OH-].[K+].Cl>>[NH2:4][C:3]1[O:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14](=[O:15])[C:2]=1[C:1]#[N:5]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8010Malononitrile2×HCID 14797Potassium HydroxideHCID 14798Sodium Hydroxide2×HCID 796682-Acetoxybenzoyl chloride

Product 1

HCID 123420572-Amino-4-oxo-4H-1-benzopyran-3-carbonitrile

Conditions

Temperature
40 °C

Procedure

-- A mixture of 6.6 g (0.1 mole) of malononitrile, 50 g of ice, 5 ml of 20% sodium hydroxide and 9.9 g (0.5 mole) of 2-acetoxy benzoyl chloride is stirred vigorously for 10 minutes. Second portions of malononitrile and 20% sodium hydroxide are added, the mixture is stirred another 10 minutes, then warmed to 40°C. With stirring, there is added 50% potassium hydroxide solution in 5 ml increments until the solution becomes clear. The solution is cooled, acidified with conc. HCl, and the solid filtered and washed with water and air dried, mp 315°-20°C.

Workup

  1. stirringthe mixture is stirred another 10 minutes
  2. stirringWith stirring
  3. temperatureThe solution is cooled
  4. filtrationthe solid filtered
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-8e0865b639e64962bcd14b9db75895dd
Source dataset
uspto-grants-1976_01
Patent number
US03932466

Reaction notes

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