Reaction #155311

Reaction equation

Meldrum's acid

methyl orthoformate

3-Propoxynaphthalen-2-ylamine

→

2,2-dimethyl-5-[(3-propoxynaphthalen-2-ylamino) methylene][1,3]dioxane-4,6-dione

Yield 95.0%

Conditions

Workup

1. 1
   Temperaturewhile heating
2. 2
   Temperatureunder reflux
3. 3
   workup.STIRRINGthe resulting mixture was stirred for 4 hours
4. 4
   Temperaturewhile heating
5. 5
   Temperatureunder reflux
6. 6
   Concentrationconcentrated to dryness under reduced pressure
7. 7
   Otherto recrystallize the residue from methanol

Procedure

Meldrum's acid (2.59 g, 17.9 mmol) was added to methyl orthoformate (16 ml), and the mixture was stirred for 2 hours while heating under reflux. 3-Propoxynaphthalen-2-ylamine (2.5 g, 12.4 mmol) was added thereto, and the resulting mixture was stirred for 4 hours while heating under reflux. The reaction mixture was cooled to room temperature and then concentrated to dryness under reduced pressure to recrystallize the residue from methanol, giving a pale brown powder of 2,2-dimethyl-5-[(3-propoxynaphthalen-2-ylamino) methylene][1,3]dioxane-4,6-dione (4.19 g, yield: 95%).

Source