Hydrochloric Acid → 5-(3-Chloro-phenyl)-3,3-diethyl-1,3-dihydro-indol-2-one

HRID 990643ノート

反応式

HRID 990643 の反応式
[CH2:1]([C:3]1[C:4](=[O:12])[N:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2].[CH2:13]([Li])[CH2:14][CH2:15][CH3:16].CN(C)[CH2:20][CH2:21]N(C)C.I[CH2:27][CH3:28].[ClH:29]>C1COCC1>[Cl:29][C:14]1[CH:15]=[C:16]([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][C:4](=[O:12])[C:3]3([CH2:20][CH3:21])[CH2:1][CH3:2])[CH:27]=[CH:28][CH:13]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 219862793-Ethylindol-2-oneHCID 178418339Butyllithium

生成物 1

HCID 99482465-(3-Chloro-phenyl)-3,3-diethyl-1,3-dihydro-indol-2-one収率 45%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-ethylindol-2-one (16 g, 0.1 mol) in dry THF (200 ml) under N2 was cooled to −25° C. and treated drop wise with n-butyllithium (2.5M in hexanes, 80 ml, 0.2 mol). To the resulting solution was added N,N,N′,N′-tetramethylethylenediamine (30 ml, 0.2 mol). After 30 min. iodoethane (8 ml, 0.1 mol) was added and the reaction rnixture was allowed to warm to RT and stirred over night. The reaction mixture was poured into an aqueous HCl solution, extracted with EtOAc (2×) and the combined organic layers were washed with dil. HCl, water, brine, dried (MgSO4) and concentrated. The residual oil was triturated with hexane to afford the title product (9 g, 45%), mp. 156-159° C. 1H NMR (DMSO-d6) δ 10.44 (s, 1H), 7.70-7.69 (t, 1H), 7.62-7.59 (m, 1H), 7.58 (d, 1H J=1.7 Hz), 7.53-7.50 (m, 1H), 7.45-7.41 (t, 1H), 7.36-7.35 (m, 1H), 7.34-7.33 (m, 1H), 6.91-6.89 (d, 1H J=8.2 Hz), 1.87-1.80 (m, 2H), 1.77-1.70 (m, 2H), 0.54-0.50 (t, 6H); MS (+ESI) m/z 190 (M+H).

後処理

  1. extractionextracted with EtOAc (2×)
  2. washthe combined organic layers were washed with dil. HCl, water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residual oil was triturated with hexane

出典と根拠

ORDレコード
ord-a0dc37b3a01e44b29e9052bcbabeb776
出典データセット
uspto-grants-2002_10
特許番号
US06462032B1

反応ノート

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