Acetic Acid → HCID 178476384, compound

HRID 1977196Notes

Reaction equation

HRID 1977196 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 with water 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).

Workup

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

Sources & evidence

ORD record
ord-9406f6ef89c441b49c929eedb8e10a5c
Source dataset
uspto-grants-2001_05
Patent number
US06232313B1

Reaction notes

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