Hydrochloric Acid → 1-Amino-2-[3-(3-formylphenoxy)propylamino]-1-cyclobutene-3,4-dione

HRID 1651345Notes

Reaction equation

HRID 1651345 reaction equation
[NH2:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]2OCC[O:20]2)[CH:14]=1.Cl>C(O)C>[NH2:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[O:20])[CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 230519051-Amino-2-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propylamino}-1-cyclobutene-3,4-dione

Product 1

HCID 230519081-Amino-2-[3-(3-formylphenoxy)propylamino]-1-cyclobutene-3,4-dioneYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 1-amino-2-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propylamino}-1-cyclobutene-3,4-dione (11.66 g, 0.037 mole) was suspended in a solution of 200 mL of 95% ethanol and 20 mL of aqueous 2.0N HCl. The suspension was stirred at ambient temperature for 2 hours, then filtered (slowly) and dried in vacuo to give 9.85 g of crude title compound. Recrystallization from 150 mL of 95% ethanol and 35 mL of aqueous 1N HCl yielded 5.74 g of purified title compound; mp=203°-206° C.

Workup

  1. filtrationfiltered (slowly) and
  2. customdried in vacuo

Sources & evidence

ORD record
ord-a83bffc917204d8faa1b43dc4019f58f
Source dataset
uspto-grants-1990_05
Patent number
US04927968

Reaction notes

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