Ethyl 4-(4-nitrophenyl)-4-oxobutanoate → ethyl 4-(4-aminophenyl)-4-oxobutanoate

HRID 2258693ノート

反応式

HRID 2258693 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:9]=1

参加物

4

反応物 1

HCID 15535281Ethyl 4-(4-nitrophenyl)-4-oxobutanoate

生成物 1

HCID 232338ethyl 4-(4-aminophenyl)-4-oxobutanoate収率 30.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of ethyl 4-(4-nitrophenyl)-4-oxobutyrate (1.4 g, 5.6 mmol) and 10% palladium on carbon (0.18 g) in ethanol (50 ml) was shaken under hydrogen (50 psi) for 2 hours then filtered and concentrated in vacuo. The residue was absorbed onto silica gel (5 g) from an ethyl acetate solution and purified by chromatography on silica gel (100 g) eluting with ethyl acetate:hexane (1:2) to give ethyl 4-(4-aminophenyl)-4-oxobutyrate (0.38 g) as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ: 1.17 (t, J=7 Hz, 3H, CH3), 2.56 (t, J=6.5 Hz, 2H, CH2), 3.10 (t, J=6.5 Hz, 2H, CH2), 4.04 (q, J=7 Hz, ester CH2), 6.04 (br s, 2H, NH2), 6.57 (d, J=9 Hz, 2H, Ar), 7.69 (d, J=9 Hz, 2H, Ar). Anal. Calculated for C12H15NO3 :C, 65.I4; H, 6.83; N, 6.33. Found: C, 65.23; H, 6.85; N, 6.32.

後処理

  1. filtrationthen filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was absorbed onto silica gel (5 g) from an ethyl acetate solution
  4. custompurified by chromatography on silica gel (100 g)
  5. washeluting with ethyl acetate:hexane (1:2)

出典と根拠

ORDレコード
ord-299413afb7bc4b8c9c3b4f5952e2a021
出典データセット
uspto-grants-1997_08
特許番号
US05661155

反応ノート

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