Acetic Acid → Ppo-IN-7

HRID 235576Notes

Reaction equation

HRID 235576 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][C:13]#[CH:14])[C:6]=2[CH:15]=1.[C:16]1(=O)[O:21][C:19](=[O:20])[C:18]2[CH2:22][CH2:23][CH2:24][CH2:25][C:17]1=2.C(O)(=O)C>O>[CH2:12]([N:7]1[C:6]2[CH:15]=[C:2]([N:1]3[C:19](=[O:20])[C:18]4[CH2:22][CH2:23][CH2:24][CH2:25][C:17]=4[C:16]3=[O:21])[CH:3]=[CH:4][C:5]=2[O:10][CH2:9][C:8]1=[O:11])[C:13]#[CH:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 136490056-amino-4-propargyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 11169020Ppo-IN-7Yield 30.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-amino-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (0.8 g), 3,4,5,6-tetrahydrophthalic anhydride (0.61 g) and acetic acid (20 ml) was heated under reflux for 2 hours. After being allowed to cool, water was added to the mixture, and the precipitated crystals were collected by filtration and washed with water. Recrystallization from ethanol gave 2-[4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.4 g). m.p., 205°-206° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with water
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-a09cb6f5d6304c2cb1fa03b92e3c7e74
Source dataset
uspto-grants-1987_02
Patent number
US04640707

Reaction notes

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