Water → HCID 14099186, compound

HRID 568746Notes

Reaction equation

HRID 568746 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH3:14])[C:6]=2[CH:15]=1.[CH3:16][C:17]1[C:18]([O:20][C:21](=O)[C:22]=1[CH3:23])=[O:19].O>C(O)(=O)C>[CH2:12]([N:7]1[C:6]2[CH:15]=[C:2]([N:1]3[C:18](=[O:19])[C:17]([CH3:16])=[C:22]([CH3:23])[C:21]3=[O:20])[CH:3]=[CH:4][C:5]=2[O:10][CH2:9][C:8]1=[O:11])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 13010Dimethylmaleic anhydrideHCID 136655946-Amino-4-propyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 14099186HCID 14099186, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.27 g of 6-amino-4-propyl-2H-1,4-benzoxazin-3(4H)-one and 1.7 g of 2,3-dimethylmaleic anhydride were refluxed for 2 hours in acetic acid. After the reaction mixture was allowed to cool, 50 ml of water was added, and the precipitated crystals were collected by filtration and recrystallized from ethanol to give 1.7 g of 1-[4-propyl-2H-1,4-benzoxazin-3(4H)-on-6-yl]-3,4-dimethyl-2,5-dioxo-2,5-dihydropyrrole. m.p. 147°-149° C.

Workup

  1. temperatureto cool
  2. filtrationthe precipitated crystals were collected by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-24774bd72c354adc9d618411ed14612b
Source dataset
uspto-grants-1988_03
Patent number
US04729784

Reaction notes

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