Acetic Acid → HCID 166499, compound
Reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:4][CH:3]=1.C1N2CN3CN(C2)CN1C3.[C:26](O)(=[O:28])C>>[CH:26]([C:3]1[CH:4]=[C:5]([S:12]([OH:15])(=[O:14])=[O:13])[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:11]=2[C:2]=1[OH:1])=[O:28]Participants
4
Procedure
8-Hydroxyquinoline-5-sulfonic acid monohydriate (0.015 mol, 3.65 g), hexamethylenetetramine (0.225 mol, 21.0 g) and acetic acid (750 mL) were stirred and heated at 97°-100° C. for 6 hrs. After cooling, acetic acid was removed under reduced pressure, and the residue was treated with acetone (1 L) to give a precipitate which was filtered off and washed with additional acetone. Water (30 mL) and concentrated hydrochloric acid (15 mL) were then added to the solid. The resulting solution was refluxed for 2 hours. Then, the mixture was concentrated under reduced pressure and left for crystallization. The solid was filtered off, washed with water and dried to give pure 7-formyl-8-hydroxyquinoline-5-sulfonic acid in 45% yield.
Workup
- temperatureheated at 97°-100° C. for 6 hrs
- temperatureAfter cooling
- customacetic acid was removed under reduced pressure
- additionthe residue was treated with acetone (1 L)
- customto give a precipitate which
- filtrationwas filtered off
- washwashed with additional acetone
- additionWater (30 mL) and concentrated hydrochloric acid (15 mL) were then added to the solid
- temperatureThe resulting solution was refluxed for 2 hours
- concentrationThen, the mixture was concentrated under reduced pressure
- waitleft for crystallization
- filtrationThe solid was filtered off
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-a108d13379664f2cbe270f0d8aff136b
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05681832
Reaction notes
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