4-Nitrobenzoic Acid → Benzoic acid, p-nitro-, acetylhydrazide

HRID 1665621Notes

Reaction equation

HRID 1665621 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[N+:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=1)([O-:22])=[O:21].CCN=C=NCCCN(C)C.Cl.[C:44]([NH:47][NH2:48])(=[O:46])[CH3:45]>CN(C=O)C.O>[C:44]([NH:47][NH:48][C:27](=[O:29])[C:26]1[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:31][CH:30]=1)(=[O:46])[CH3:45]

Participants

8

Reactant 5

HCID 61084-Nitrobenzoic AcidHCID 14039AcetohydrazideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 3332418Benzoic acid, p-nitro-, acetylhydrazideYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (972 mg, 7.2 mmol) and DIEA (1.14 g, 8.9 mmol) were added to a stirred solution of 4-nitro-benzoic acid (1 g, 5.96 mmol) in DMF (6 mL). The reaction mixture was cooled to 10° C. EDCI.HCl (1.38 g, 7.2 mmol) followed by acetic acid hydrazide (490 mg, 6.6 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water and the product extracted with ethyl acetate. The organics were washed with saturated sodium bicarbonate solution followed by brine solution, dried over Na2SO4 and evaporated to afford 700 mg (55%) of 4-nitro-benzoic acid N′-acetyl-hydrazide. 1H NMR: (DMSO-d6): δ 10.7 (s, 1H), 10.0 (s, 1H), 8.4 (d, 2H), 8.1 (d, 2H), 1.9 (s, 3H).

Workup

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe organics were washed with saturated sodium bicarbonate solution
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-a967c90b530c42d38c515ff643f4ccc2
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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