Ethyl Acetate → HCID 178518779, compound

HRID 2294197Notes

Reaction equation

HRID 2294197 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([OH:12])[C:6]3[C:13](=O)[O:14][CH:15](O)[C:5]=3[C:4]=2[C:3]=1[Cl:18].O.[NH2:20][NH2:21].C(OCC)(=O)C>CS(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([OH:12])[C:6]3[C:13](=[O:14])[NH:20][N:21]=[CH:15][C:5]=3[C:4]=2[C:3]=1[Cl:18]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 178519217HCID 178519217, compound

Product 1

HCID 178518779HCID 178518779, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.9 g (0.010 mol) of (RS)-8,9-dichloro-1,4-dihydroxy-1,3-dihydro-furo[3,4-c]quinolin-3-one were dissolved in 60 ml of dimethyl sulphoxide while gassing with argon. 0.51 g (0.010 mol) of hydrazine hydrate was added thereto and the mixture was stirred at room temperature for 50 hrs. An orange coloured solution was obtained and this was treated with 300 ml of ethyl acetate. The precipitated product was filtered off under suction, rinsed with ethyl acetate and recrystallized from dimethylformamide/ethyl acetate. Yield: 0.70 g (25%) of 9,10-dichloro-5-hydroxy-3,4-dihydro-pyridazino[4,5-c]quinolin-4-one as yellow-orange coloured crystals; m.p. ~270° C.

Workup

  1. customwas obtained
  2. filtrationThe precipitated product was filtered off under suction
  3. washrinsed with ethyl acetate
  4. customrecrystallized from dimethylformamide/ethyl acetate

Sources & evidence

ORD record
ord-3bc36569c58d483bbb6c3223e85f3784
Source dataset
uspto-grants-1997_11
Patent number
US05688803

Reaction notes

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