Methylhydrazine → HCID 178481737, compound

HRID 1748821Notes

Reaction equation

HRID 1748821 reaction equation
O=[C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:3][C:4](OCC)=[O:5].[CH3:15][NH:16][NH2:17]>CCO>[CH3:15][N:16]1[C:4]([OH:5])=[CH:3][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:17]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 2736461Ethyl 3-oxo-3-(pyridin-2-yl)propanoate

Product 1

HCID 178481737HCID 178481737, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of ethyl 3-oxo-3-(pyridin-2-yl)propanoate (25.00 g, 129 mmol, Matrix Scientific) in EtOH (60 mL) was added methylhydrazine (6.81 mL, 129 mmol). The mixture was heated at about 85° C. for about 3 h then cooled to rt and concentrated at rt under reduced pressure. The material was triturated with Et2O (40 mL). The solids were collected by filtration then washed with Et2O to give 1-methyl-3-(pyridin-2-yl)-1H-pyrazol-5-ol (17.80 g, 79%). The filtrate was concentrated under reduced pressure then the material was triturated with 1:1 DCM/Et2O. The solids were collected by filtration and washed with Et2O to give a second crop of 1-methyl-3-(pyridin-2-yl)-1H-pyrazol-5-ol (1.20 g, 5%): LC-MS (Table 1, Method g) Rt=1.05 min, m/z 176 (M+H)+; 1H-NMR (DMSO, Bruker 400 MHz) δ 11.05 (s, 1H), 8.50-8.47 (m, 1H), 7.83-7.80 (m, 1H), 7.78-7.69 (m, 1H), 7.24-7.19 (m, 1H), 5.90 (s, 1H), 3.57 (s, 3H).

Workup

  1. temperaturethen cooled to rt
  2. concentrationconcentrated at rt under reduced pressure
  3. customThe material was triturated with Et2O (40 mL)
  4. filtrationThe solids were collected by filtration
  5. washthen washed with Et2O

Sources & evidence

ORD record
ord-4274f93feedb4eafb66e06158be77451
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

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