Diethyl (ethoxymethylene)malonate → HCID 21508894, compound

HRID 1287421Notes

Reaction equation

HRID 1287421 reaction equation
CCO[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:16][CH:17]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:20]=2[O:19][CH2:18]1.[OH-].[Na+]>O>[CH3:16][CH:17]1[N:22]2[CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11](=[O:13])[C:23]3[CH:24]=[C:25]([CH3:27])[CH:26]=[C:20]([C:21]=32)[O:19][CH2:18]1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 14798Sodium HydroxideHCID 205712433,7-Dimethyl-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 21508894HCID 21508894, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

Diethyl ethoxymethylene malonate (19.8 g., 0.092 mole) is added to 3,4-dihydro-3,7-dimethyl-2H-1,4-benzoxazine (15.0 g., 0.092 mole) and the solution is heated at 110° to 120° C. for three hours. Polyphosphoric acid (100 g.) is added and the solution is gradually heated to 130° C. with occasional stirring. The solution is heated at 140° to 150° C. for one additional hour. The hot solution is poured into 300 ml. water with stirring, then neutralized with forty percent sodium hydroxide solution. The solid which precipitates is separated by filtration and washed with water. Recrystallization from ethanol gives ethyl 2,3-dihydro-3,9-dimethyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate, m.p. 195°-197° C.

Workup

  1. temperaturethe solution is heated at 110° to 120° C. for three hours
  2. temperatureThe solution is heated at 140° to 150° C. for one additional hour
  3. additionThe hot solution is poured into 300 ml
  4. customThe solid which precipitates
  5. customis separated by filtration
  6. washwashed with water
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-286d2222a38d433986b8f06b6e1c214c
Source dataset
uspto-grants-1976_10
Patent number
US03984548

Reaction notes

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