Ethyl 2-methyl-5-nitrobenzoate → Ethyl 5-amino-2-methylbenzoate

HRID 1640010ノート

反応式

HRID 1640010 の反応式
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]>C(O)C.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:2]([CH3:1])=[C:3]([CH:9]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

参加物

4

反応物 1

HCID 18510875Ethyl 2-methyl-5-nitrobenzoate

生成物 1

HCID 18690998Ethyl 5-amino-2-methylbenzoate収率 101%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of ethyl 2-methyl-5-nitrobenzoate (11.5 g, 54 mmol) and 10% Pd/C (1.2 g) in ethanol (200 mL) was shaken under an atmosphere of hydrogen at 40 psi for 18 h. After this time, the mixture was filtered through diatomaceous earth and concentrated under reduced pressure to provide ethyl 5-amino-2-methylbenzoate (9.77 g, 98%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 7.25 (d, J=2.6 Hz, 1H), 7.02 (d, J=8.1 Hz, 1H), 6.74 (d, J=8.1 Hz, 1H), 4.33 (q, J=7.2 Hz, 2H), 2.46 (s, 3H), 1.38 (t, J=7.1 Hz, 3H).

後処理

  1. filtrationAfter this time, the mixture was filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9c36d299c9b44339b779d02427b7699a
出典データセット
uspto-grants-2012_02
特許番号
US08110681B2

反応ノート

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