Sulfuric Acid → 2-(5-Chloro-6-oxo-1,6-dihydro-pyridazin-4-yloxy)-benzamide

HRID 2381349Notes

Reaction equation

HRID 2381349 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[NH:6][N:5]=[CH:4][C:3]=1[O:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].S(=O)(=O)(O)[OH:19]>>[Cl:1][C:2]1[C:7](=[O:8])[NH:6][N:5]=[CH:4][C:3]=1[O:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]([NH2:13])=[O:19]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 57919203HCID 57919203, compound

Product 1

HCID 579191932-(5-Chloro-6-oxo-1,6-dihydro-pyridazin-4-yloxy)-benzamideYield 96%

Conditions

Temperature
25 °C

Procedure

A solution of 2-(5-chloro-6-oxo-1,6-dihydro-pyridazin-4-yloxy)-benzonitrile (43.1 g, 0.17 mol) in concentrated sulfuric acid (150 mL) was stirred at 110° C. for 1 h and was then allowed to cool to 25° C. The reaction was added dropwise to ice water. The resulting precipitate was collected by filtration, washed with cold water and dried in vacuo to afford 2-(5-chloro-6-oxo-1,6-dihydro-pyridazin-4-yloxy)-benzamide (44.5 g, 96%) as a white solid; ESI-MS 266 [M+H+]; HPLC: >97% (purity). 1H-NMR (300 MHz, DMSO-d6) δ 13.38 (s, 1H), 7.81 (s, 2H), 7.62-7.65 (m, 1H), 7.47-7.55 (m, 2H), 7.33-7.38 (m, 1H), 7.24-7.27 (m, 1H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with cold water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-13c232ed5a5b418a950613ef72e29ab5
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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