Acetic Acid → HCID 178476384, compound

HRID 323607Notes

Reaction equation

HRID 323607 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-af1575badd98499da0a012a32de37465
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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