Methylhydrazine → HCID 53363532, compound

HRID 2042531Notes

Reaction equation

HRID 2042531 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:5][CH:4]=1.[CH3:16][NH:17][NH2:18]>CC(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][C:12](=[O:14])[N:17]([CH3:16])[N:18]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 766134-Methoxy-gamma-oxobenzenebutanoic acid

Product 1

HCID 53363532HCID 53363532, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a 500 mL round bottom flask, 4-(4-methoxyphenyl)-4-oxobutyric acid (27 g, 132 mmol) and methylhydrazine (7.3 g, 8.5 mL, 159 mmol) in 2-propanol (150 mL) were stirred at reflux 12 h. The solvent was concentrated to about 50 mL, ether was added (˜50 mL) and the product collected by filtration, washed 1× with ether and dried under house vacuum. Yield 27 g (94%, purity >95%), mp 133-135° C. 1H NMR (CDCl3) δ 2.57 (m, 2H), 2.9 (m, 2H), 3.4 (s, 3H), 3.8 (s, 3H), 6.9 (d, 2H), 7.6 (d, 2H). MS m/z=218 (M+H).

Workup

  1. temperatureat reflux 12 h
  2. concentrationThe solvent was concentrated to about 50 mL, ether
  3. additionwas added (˜50 mL)
  4. filtrationthe product collected by filtration
  5. washwashed 1× with ether
  6. customdried under house vacuum

Sources & evidence

ORD record
ord-0a47ef6d63064d5bb21ed80dc8b7ca9f
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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