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

HRID 1665621ノート

反応式

HRID 1665621 の反応式
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]

参加物

8

反応物 5

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

生成物 1

HCID 3332418Benzoic acid, p-nitro-, acetylhydrazide収率 55%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a967c90b530c42d38c515ff643f4ccc2
出典データセット
uspto-grants-2011_10
特許番号
US08039463B2

反応ノート

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