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

HRID 1665621노트

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HRID 1665621 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
10 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a967c90b530c42d38c515ff643f4ccc2
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039463B2

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