(4-Nitrophenyl)acetic acid → 2-(4-Nitrophenyl)acetohydrazide

HRID 1921622

反応式

HRID 1921622 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[NH2:25][NH2:26]>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:25][NH2:26])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

参加物

6

反応物 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 6228DimethylformamideHCID 9321HydrazineHCID 65578Oxalyl chloride

生成物 1

HCID 2873312-(4-Nitrophenyl)acetohydrazide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 4-nitrophenylacetic acid (2.81 mmol) in dry dichloromethane (10 mL) was treated with a 2N solution of oxalyl chloride (3.0 mL) and DMF (0.02 mL) via syringe, and the reaction stirred at ambient temperature for 1 h. The reaction was concentrated to dryness in vacuo and the crude product was dissolved in dry dichloro-methane (20 mL), treated with anhydrous hydrazine (11.1 mmol) via syringe, and stirred at ambient temperature for 18 h. The resulting suspension was filtered, solids rinsed with dichloromethane, dissolved in MeOH/CH2Cl2, filtered, and filtrate concentrated in vacuo giving the title compound as an orange solid. 1H NMR (DMSO-d6) δ 8.17 (2H, d, J=8.8 Hz,), 7.54 (2H, d, J=8.8 Hz), 3.54 (2H, s).

後処理

  1. concentrationThe reaction was concentrated to dryness in vacuo
  2. dissolutionthe crude product was dissolved in dry dichloro-methane (20 mL)
  3. stirringstirred at ambient temperature for 18 h
  4. filtrationThe resulting suspension was filtered
  5. washsolids rinsed with dichloromethane
  6. dissolutiondissolved in MeOH/CH2Cl2
  7. filtrationfiltered
  8. concentrationfiltrate concentrated in vacuo

出典と根拠

ORDレコード
ord-0db6b45f70844e0e9f4000e1585658c0
出典データセット
uspto-grants-2012_05
特許番号
US08173654B2

関連ノート

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