Acetic Acid → HCID 14279665, compound

HRID 2291772Notes

Reaction equation

HRID 2291772 reaction equation
[NH2:1][C:2]1[C:3]([F:16])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:12][C:13]#[N:14])[C:6]=2[CH:15]=1.[C:17]1(=O)[O:22][C:20](=[O:21])[CH:19]2[CH2:23][CH2:24][CH:25]=[CH:26][CH:18]12.C(O)(=O)C>O>[C:13]([CH2:12][N:7]1[C:6]2[CH:15]=[C:2]([N:1]3[C:20](=[O:21])[C:19]4[CH2:23][CH2:24][CH2:25][CH2:26][C:18]=4[C:17]3=[O:22])[C:3]([F:16])=[CH:4][C:5]=2[O:10][CH2:9][C:8]1=[O:11])#[N:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 127266013a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dioneHCID 14347817HCID 14347817, compound

Product 1

HCID 14279665HCID 14279665, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-amino-4-cyanomethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-one (0.5 g), tetrahydrophthalic anhydride (0.38 g) and acetic acid (10 ml) were mixed with each other, then the mixture was refluxed under heating for 3 hours. After the liquor was allowed to cool, it was added to water (40 ml), and separating crystals were collected by filtration, and then the crystals were dissolved in dichloromethane (30 ml). The dichloromethane solution was washed with a saturated solution of sodium bicarbonate, and water, in that order, and then dehydrated with anhydrous sodium sulfate, and subsequently concentrated. Separated crystals were washed with a small amount of ether to give the desired 2-[4-cyanomethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-on 6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.59 g). mp. 227°-229° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 3 hours
  3. temperatureto cool
  4. customseparating crystals
  5. filtrationwere collected by filtration
  6. dissolutionthe crystals were dissolved in dichloromethane (30 ml)
  7. washThe dichloromethane solution was washed with a saturated solution of sodium bicarbonate, and water, in that order
  8. concentrationsubsequently concentrated
  9. customSeparated crystals
  10. washwere washed with a small amount of ether

Sources & evidence

ORD record
ord-9fa03911a1d5483792a705c41cbef472
Source dataset
uspto-grants-1989_01
Patent number
US04798620

Reaction notes

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