Ammonia → 6-Cyano-1-(2-carbamoylvinyl)-2-naphthol

HRID 1419255Notes

Reaction equation

HRID 1419255 reaction equation
[NH3:1].[C:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([CH:14]=[CH:15][C:16](OCC)=[O:17])=[C:9]([OH:21])[CH:8]=[CH:7]2)#[N:3]>>[C:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([CH:14]=[CH:15][C:16](=[O:17])[NH2:1])=[C:9]([OH:21])[CH:8]=[CH:7]2)#[N:3]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 53697716HCID 53697716, compound

Product 1

HCID 537790446-Cyano-1-(2-carbamoylvinyl)-2-naphthol

Procedure

2.0 Liters of 25% aqueous ammonia was added to 25.2 g of 6-cyano-1-(2-ethoxycarbonylvinyl)-2-naphthol, followed by stirring at 40°-45° C. for 32 hours. After cooling, the reaction mixture was concentrated to 300 ml under reduced pressure, and the residue was stirred for 30 minutes under cooling with water. The precipitate was collected by filtration and washed with a small amount of water and acetone to obtain 9.55 g of the desired product.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated to 300 ml under reduced pressure
  3. stirringthe residue was stirred for 30 minutes
  4. temperatureunder cooling with water
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with a small amount of water and acetone

Sources & evidence

ORD record
ord-18b1e4c054544813a05ae764760e7d6d
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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