Ethanol → HCID 4331501, compound

HRID 126690Notes

Reaction equation

HRID 126690 reaction equation
[O:1]=[C:2]1[C:11]2[C:6]3[C:7](=[CH:12][CH:13]=[CH:14][C:5]=3[C:4](=[O:15])[N:3]1[CH2:16][C:17]([OH:19])=[O:18])[CH:8]=[CH:9][CH:10]=2.O.[C:21]1(C)C=CC(S(O)(=O)=O)=C[CH:22]=1.C(O)C>C1(C)C=CC=CC=1>[CH2:21]([O:18][C:17](=[O:19])[CH2:16][N:3]1[C:4](=[O:15])[C:5]2[CH:14]=[CH:13][CH:12]=[C:7]3[C:6]=2[C:11](=[CH:10][CH:9]=[CH:8]3)[C:2]1=[O:1])[CH3:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 2120AlrestatinHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 4331501HCID 4331501, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mechanically-stirred mixture of 1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid (125.0 g, 0.49 mole), p-toluenesulfonic acid hydrate (9.3 g, 0.049 mole), anhydrous pure ethanol (226 g, 288 ml, 0.49 mole) and dry toluene (750 ml) was heated at reflux for 16 hr in a Soxhlet apparatus in which the thimble was filled with hydrated alkali-aluminium silicate (3 A Molecular Sieves). The title compound was crystallized from the reaction mixture after cooling to room temperature. The crystals were collected and a second crop of crystals were obtained from the mother liquors. Recrystallization of the two crops of crystals from ethyl acetate gave the title compound; mp 160°-162° C.; UV (MeOH) 232, 332 and 341 nm, ε=48,613, 13,470 and 12,920, respectively; IR (CHCl3) 1745, 1705 and 1665 cm-1 ; Anal. Calc'd.: C, 67.84%; H, 4.63%; N, 4.94%; Found: C, 67.89%; H, 4.60 %; N, 4.87%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hr in a Soxhlet apparatus in which the thimble
  3. customThe title compound was crystallized from the reaction mixture
  4. customThe crystals were collected
  5. customa second crop of crystals were obtained from the mother liquors
  6. customRecrystallization of the two crops of crystals from ethyl acetate

Sources & evidence

ORD record
ord-f12a30e48db94c11b6c8e5c852db714e
Source dataset
uspto-grants-1981_03
Patent number
US04254108

Reaction notes

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