Hydrazine hydrate (1:1) → 2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetohydrazide

HRID 579216Notes

Reaction equation

HRID 579216 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH2:13][CH3:14])[C:7]=1[C:15](=[O:21])[C:16](OCC)=[O:17])[CH3:5]>CO>[CH2:4]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH2:13][CH3:14])[C:7]=1[C:15](=[O:21])[C:16]([NH:2][NH2:3])=[O:17])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 56942718Ethyl (2,6-diethyl-4-methylphenyl)glyoxylate

Product 1

HCID 569428732-(2,6-Diethyl-4-methylphenyl)-2-oxoacetohydrazideYield 39.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
2 °C

Procedure

To a 100 ml volume four-necked flask, methanol (22.91 g) and hydrazine hydrate (1.93 g) were added at room temperature, and cooled. Ethyl 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetate (9-a) (5.01 g) diluted with methanol (10.02 g) was added dropwise at 1° C. over 5 minutes. The resulting mixture was stirred at 2° C. for 4 hours, then the mixture was filtered. The resulting filtrate was concentrated, added tert-butyl methyl ether (41 g), and washed with brine (14 g). The resulting organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography (silica gel: 40 g, hexane: ethyl acetate=1:1) to gave 1.88 g of 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetohydrazide ((12-1)-(11)-39).

Workup

  1. temperaturecooled
  2. additionwas added dropwise at 1° C. over 5 minutes
  3. filtrationthe mixture was filtered
  4. concentrationThe resulting filtrate was concentrated
  5. additionadded tert-butyl methyl ether (41 g)
  6. washwashed with brine (14 g)
  7. dry with materialThe resulting organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2125adbca454ff780c9bf3987791da2
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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