Hydrazine → 4-Isobutylbenzohydrazide

HRID 2242234Notes

Reaction equation

HRID 2242234 reaction equation
[CH2:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1C(O)=O)[CH:2]([CH3:4])[CH3:3].CN([C:17]([O:21]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:47][NH2:48]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([C:5]1[CH:6]=[CH:10][C:11]([C:17]([NH:47][NH2:48])=[O:21])=[CH:12][CH:13]=1)[CH:2]([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 142242462-(2-Methylpropyl)benzoic acid

Product 1

HCID 207719354-IsobutylbenzohydrazideYield 97.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution isobutylbenzoic acid (2.00 g, 11.2 mmol) in DMF (10 ml) was treated with HBTU (4.25 g, 11.2 mmol), diisopropylethylamine (7.24 g, 56.0 mmol), then hydrazine (1.80 g, 56.0 mmol) and stirred at room temperature for 12 hours. The reaction was diluted with ethyl acetate (150 mL), washed with 5% NaHCO3 (aq.) and brine, dried (MgSO4), filtered and concentrated in vacuo to give the title compound (2.10 g, 91%) as a white solid.

Workup

  1. washwashed with 5% NaHCO3 (aq.) and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f74de978b2af496aa62102ed97e889a8
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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