Ammonium Hydroxide → 6-Chloro-5-phenylpyridazin-3-amine

HRID 2239838Notes

Reaction equation

HRID 2239838 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH4+:15].[OH-]>>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH2:15])=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 113220803,6-Dichloro-4-phenylpyridazine

Product 1

HCID 569536546-Chloro-5-phenylpyridazin-3-amineYield 56%

Conditions

Temperature
140 °C

Procedure

3,6-dichloro-4-phenylpyridazine (J. Med. Chem. 2005, 48, 7089; 5.93 g, 26.3 mmol) was divided into 6 microwave tubes, and concentrated NH4OH (7 mL) was added to each. After sealing, each was heated at 140° C. for 1 h. The microwave tubes were uncapped, the precipitates were filtered and washed with cold water. The precipitates from all reactions were combined, and Et2O (150 mL) was added. After stirring overnight, the remaining solid was filtered, rinsed with Et2O and dried to give 6-chloro-5-phenylpyridazin-3-amine (3.06 g, 56%)

Workup

  1. additionwas added to each
  2. filtrationthe precipitates were filtered
  3. washwashed with cold water
  4. customThe precipitates from all reactions
  5. additionEt2O (150 mL) was added
  6. filtrationthe remaining solid was filtered
  7. washrinsed with Et2O
  8. customdried

Sources & evidence

ORD record
ord-b7181fd2110a4144a16aa41d9fc12191
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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