Methyl 4-aminobenzoate → Methyl 4-hydrazinylbenzoate

HRID 508724

反応式

HRID 508724 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[N:12]([O-])=O.[Na+]>Cl>[NH:1]([C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[NH2:12]

参加物

4

反応物 2

HCID 12082Methyl 4-aminobenzoateHCID 23668193Sodium Nitrite

生成物 1

HCID 408928Methyl 4-hydrazinylbenzoate収率 93,853.602%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

To a cold solution of methyl 4-aminobenzoate (15.0 g, 0.099 mol) in conc. HCl was added aq. solution of sodium nitrite (7.5 g, 0.109 mmol) at 0-5° C. The reaction mass was stirred at RT for 1-2 h. The reaction mass was cooled to 0° C. and stannous chloride (0.049 g, 0.210 mmol) was added and further stirred at RT for 2-3 h. The reaction mass was filtered to afford 17.0 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.77 (s, 3H), 7.03 (d, J=8.4 Hz, 2H), 7.82 (d, J=8.4 Hz, 2H), 10.69 (br s, 2H); MS (m/z): 167.28 (M+H)+.

後処理

  1. temperatureThe reaction mass was cooled to 0° C.
  2. stirringfurther stirred at RT for 2-3 h
  3. filtrationThe reaction mass was filtered

出典と根拠

ORDレコード
ord-85d1bb276858455f8ce94784fe610541
出典データセット
uspto-grants-2015_08
特許番号
US09096545B2

関連ノート

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