Methanol → HCID 21071398、化合物

HRID 1371919ノート

反応式

HRID 1371919 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])([O-])=O.CO>O=[Pt]=O.C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][N:15]1[C:16](=[O:25])[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]1=[O:24]

参加物

5

反応物 2

HCID 887MethanolHCID 227222762-[2-(5-Nitro-1H-indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione

生成物 1

HCID 21071398HCID 21071398、化合物

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Combine a mixture of 2-(2-(5-nitro-1H-indol-3-yl)ethyl)isoindole-1,3-dione (1.8 g, 5.4 mmol), PtO2 (500 mg), 100 mL MeOH and 100 mL THF and hydrogenate at atmospheric pressure overnight. Filter the reaction through a pad of celite and concentrate to dryness. Redissolve the residue in 50/50 chloroform/dichloromethane and refilter through a pad of celite. Concentration under vacuum give the title compound as a dark solid: ISMS 306 (M+1); Analysis for C18H13N3O4 0.1C7H8 0.2 dichloromethane: calcd: C, 68.70; H, 4.89; N, 12.58; found: C, 69.08; H, 4.75; N, 12.69; 1H NMR (CDCl3) 7.9–7.8 (m, 3H), 7.75–7.65 (m, 2H), 7.2–7.1 (m, 1H), 7.05–7.0 (m, 2H), 6.7–6.6 (m, 1H), 4.0–3.9 (m, 2H), 3.4 (bs, 2H), 3.1–3.0 (m, 2H).

後処理

  1. customhydrogenate at atmospheric pressure overnight
  2. filtrationFilter
  3. customthe reaction through a pad of celite
  4. concentrationconcentrate to dryness
  5. dissolutionRedissolve the residue in 50/50 chloroform/dichloromethane and refilter through a pad of celite
  6. concentrationConcentration under vacuum

出典と根拠

ORDレコード
ord-e30219c9945143ddb14676365a6ecbe3
出典データセット
uspto-grants-2007_01
特許番号
US07157488B2

反応ノート

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