Succinic anhydride → HCID 5205499, compound

HRID 1090306Notes

Reaction equation

HRID 1090306 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[O:3]1.[C:13]1(=[O:19])[O:18][C:16](=[O:17])[CH2:15][CH2:14]1.[Cl-].[Al+3].[Cl-].[Cl-]>CN(C)C=O>[O:19]=[C:13]([C:10]1[CH:11]=[CH:12][C:4]2[O:3][CH:2]([CH3:1])[C:7](=[O:8])[NH:6][C:5]=2[CH:9]=1)[CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 3017302-methyl-2H-1,4-benzoxazin-3(4H)-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5205499HCID 5205499, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3,4-Dihydro-2-methyl-3-oxo-1,4(2H)-benzoxazine (11.4 g) and succinic anhydride (7 g) were added to 93 g of aluminum chloride and 15.3 ml of dimethylformamide. The mixture was stirred at 70° C. for 2.5 hours and then poured onto ice, giving a solid which was collected by filtration and washed with water. Drying under vacuum gave 16.5 g of the title compound (90% yield), mp 198°-200° C.

Workup

  1. additionpoured onto ice
  2. customgiving a solid which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customDrying under vacuum

Sources & evidence

ORD record
ord-2efa08c4b1ab42c986a637701659c781
Source dataset
uspto-grants-1992_01
Patent number
US05081242

Reaction notes

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