Hydrazine hydrate (1:1) → HCID 178432134, compound

HRID 869676Notes

Reaction equation

HRID 869676 reaction equation
[CH3:1][C:2]1[C:3]([C:12](=O)[CH2:13][C:14]#[N:15])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.O.[NH2:18][NH2:19].C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(O)C.O>[CH3:1][C:2]1[C:3]([C:12]2[CH:13]=[C:14]([NH2:15])[NH:19][N:18]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 67397893HCID 67397893, compound

Product 1

HCID 178432134HCID 178432134, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 3-(3-methylquinoxalin-2-yl)-3-oxopropanenitrile (45.8 g, 217 mmol) and hydrazine monohydrate (15.8 mL, 325 mmol) in acetic acid (109 mL) and ethanol (1083 mL) was refluxed for 17 h. After being cooled to ambient temperature, the reaction mixture was diluted with water (360 mL) and basified to pH 8 with sodium bicarbonate. The resulting precipitate was collected and washed with diisopropyl ether. The crude was diluted with methanol (1077 mL) and potassium carbonate (29.9 g), and then heated at 60° C. for 2 h. The precipitate was collected and washed with diisopropyl ether to give 3-(3-methylquinoxalin-2-yl)-1H-pyrazol-5-amine. MS (APCI): m/z 226 (M+H).

Workup

  1. temperaturewas refluxed for 17 h
  2. customThe resulting precipitate was collected
  3. washwashed with diisopropyl ether
  4. additionThe crude was diluted with methanol (1077 mL) and potassium carbonate (29.9 g)
  5. temperatureheated at 60° C. for 2 h
  6. customThe precipitate was collected
  7. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-3df8457ac8c84cd3ab0e48f7ef693f10
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

Loading…