Acetic Acid → HCID 19855750, compound

HRID 2073703Notes

Reaction equation

HRID 2073703 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[S:8]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22](=[O:23])[CH:21]=[C:20]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:19]2)=[CH:14][CH:13]=1)([OH:11])(=[O:10])=[O:9].[C:31]([OH:34])(=O)[CH3:32]>>[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:1][C:2]1[C:21]2[C:22](=[O:23])[N:18]([C:15]3[CH:14]=[CH:13][C:12]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:17][CH:16]=3)[NH:19][C:20]=2[N:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:31](=[O:34])[CH:32]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 86743872HCID 86743872, compound

Product 1

HCID 19855750HCID 19855750, compound

Procedure

1-(4-Sulfophenyl)-3-anilinopyrazolin-5-one triethylamine salt (8.6 g) and 3.5 g of ethyl acetacetate were added to 50 ml of glacial acetic acid and refluxed with heating for 8 hours, and then the reaction solution was concentrated to about 1/3 of the volume. Isopropanol (80 ml) was added thereto to deposit crystals which was then recrystallized from methanol to obtain 3.5 g of 4-methyl-7-phenyl-2-(4-sulfophenyl)pyrazolo[3,4-b]pyridine-3,6-dione triethylamine salt. These crystals (3 g), 0.9 g of glutacondialdehyde dianil hydrochloride, 1.3 ml of triethylamine, 1.1 ml of acetic anhydride and 20 ml of N,N-dimethylformamide were mixed and stirred at room temperature for one hour and then at 50° C. for 2 hours. The reaction solution was cooled to room temperature and a solution of 1.8 g of potassium acetate in 10 ml of methanol, followed by one hour stirring. The deposited crystals were recovered by filtration and recrystallized from a methanol-water mixed solvent (methanol/water=3/1) to obtain 1.1 g of Compound 33 as dark bluish, green crystals. Melting point 300° C. or more, λmaxCH3OH =767 nm.

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 8 hours
  3. concentrationthe reaction solution was concentrated to about 1/3 of the volume
  4. additionIsopropanol (80 ml) was added
  5. customto deposit crystals which was then recrystallized from methanol

Sources & evidence

ORD record
ord-2b9300ca0d964562993e4506e92f6bdb
Source dataset
uspto-grants-1990_04
Patent number
US04920031

Reaction notes

Loading…