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

HRID 68129

Reaction equation

HRID 68129 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH:11]([O-])([O-])OC.[CH2:16]([O:19][C:20]1[C:21]([NH2:30])=[CH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17][CH3:18]>>[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[C:6](=[CH:11][NH:30][C:21]2[C:20]([O:19][CH2:16][CH2:17][CH3:18])=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[C:4](=[O:5])[O:3]1

Participants

4

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 212799043-Propoxynaphthalen-2-ylamineHCID 53629101Methylorthoformate

Product 1

HCID 584924632,2-Dimethyl-5-[(3-propoxynaphthalen-2-ylamino) methylene][1,3]dioxane-4,6-dioneYield 95%

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%).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. stirringthe resulting mixture was stirred for 4 hours
  4. temperaturewhile heating
  5. temperatureunder reflux
  6. concentrationconcentrated to dryness under reduced pressure
  7. customto recrystallize the residue from methanol

Sources & evidence

ORD record
ord-18a1966deec047d38bc37b60ccbf4c99
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Linked notes

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