Acetic Acid → HCID 178476384, compound

HRID 1600027Notes

Reaction equation

HRID 1600027 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:21])[C:7]3[C:15](=[O:16])[N:14]([CH2:17][CH2:18][OH:19])[N:13]=[C:12]([OH:20])[C:8]=3[NH:9][C:10]=2[CH:11]=1.Br.[C:23](O)(=[O:25])[CH3:24]>O>[C:23]([O:19][CH2:18][CH2:17][N:14]1[C:15](=[O:16])[C:7]2[C:6](=[O:21])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:10]=3[NH:9][C:8]=2[C:12]([OH:20])=[N:13]1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 178515082HCID 178515082, compound

Product 1

HCID 178476384HCID 178476384, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An orange suspension of 7-chloro-4-hydroxy-2-(2-hydroxyethyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (0.250 g, 0.81 mM) in a 30% solution of hydrobromic acid in glacial acetic acid (5 mL) was gently refluxed for 16 hours under nitrogen. The mixture was cooled to room temperature and diluted with water (20 mL) to form a precipitate. The collected solids were washed withwater and methanol and then dried to give the title compound (0.242 g, 86%)as a tan solid, mp=307°-309° C.; MS(CI): 350 (M+H). Analysis for C15H12ClN3O5 ·0.2 CH3CO2H:Calculated: C, 51.10, H, 3.57; N, 11.60; Found: C, 50.81; H, 3.45; N, 11.86; NMR: 12.64 (br s, 1H, exchangeable), 11.91 (br s, 1H, exchangeable), 8.14 (d, J=8.64 Hz, 1H), 8.02 (d, J=1.74 Hz, 1H,), 7.43 (dd, J=1.74, 8.64 Hz), 4.32 (t, J=5.54 Hz, 2H), 4.13 (t, J=5.54 Hz), 1.98 (s, 3H).

Workup

  1. temperaturewas gently refluxed for 16 hours under nitrogen
  2. customto form a precipitate
  3. washThe collected solids were washed withwater and methanol
  4. customdried

Sources & evidence

ORD record
ord-3fb5cd26f61549e397e895280e3542c0
Source dataset
uspto-grants-1998_04
Patent number
US05744471

Reaction notes

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