3-Methylbutanal → HCID 12137096, compound

HRID 535695Notes

Reaction equation

HRID 535695 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH:4]=O.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14]N)=[CH:10][CH:9]=1>C(O)(=O)C>[Br:7][C:8]1[CH:13]=[C:12]2[C:11](=[CH:10][CH:9]=1)[NH:14][CH:4]=[C:3]2[CH:2]([CH3:6])[CH3:1]

Participants

4

Reactant 2

HCID 115523-MethylbutanalHCID 121584-Bromophenylhydrazine

Product 1

HCID 12137096HCID 12137096, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

3-Methylbutanal (0.921 g, 10.69 mmol) was added to a solution of (4-bromophenyl)hydrazine (2 g, 10.69 mmol) in acetic acid (100 mL) at 80° C., and the mixture was stirred for 3 h at 120° C. The reaction mixture was concentrated to get the residue, and the residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with saturated bicarbonate solution and brine, dried over sodium sulphate and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography using 2% ethyl acetate in pet ether to afford title compound (1.1 g, 38.4%) as an oil. 1H NMR (400 MHz, CDCl3): δ 7.91 (bs, 1H), 7.76 (m, 1H), 7.25-7.20 (m, 2H), 6.95 (d, J=2.4 Hz, 1H), 3.18-3.11 (m, 1H), 1.35 (d, J=6.8 Hz, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto get the residue
  3. customthe residue was partitioned between ethyl acetate and water
  4. customOrganic layer was separated
  5. washwashed with saturated bicarbonate solution and brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. custompurified by flash chromatography

Sources & evidence

ORD record
ord-3bfc023369da42c59fa84a3bf33be1d3
Source dataset
uspto-grants-2014_10
Patent number
US08859536B2

Reaction notes

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