Toluene → 1,5-Diamino-6-methyl-2-anthraquinonecarboxylic acid p-heptylphenyl ester

HRID 65177ノート

反応式

HRID 65177 の反応式
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([C:17]2[CH:30]=[CH:29][C:28]3[C:27](=[O:31])[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH3:35])[C:25]=4[N+:32]([O-])=O)[C:20](=[O:36])[C:19]=3[C:18]=2[NH2:37])=[O:16])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C1(C)C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]([C:17]2[CH:30]=[CH:29][C:28]3[C:27](=[O:31])[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH3:35])[C:25]=4[NH2:32])[C:20](=[O:36])[C:19]=3[C:18]=2[NH2:37])=[O:16])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

参加物

6

反応物 3

HCID 1140TolueneHCID 54519986HCID 54519986、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 540343611,5-Diamino-6-methyl-2-anthraquinonecarboxylic acid p-heptylphenyl ester

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A suspension of 0.426 g of 1-amino-6-methyl-5-nitro-2-anthraquinonecarboxylic acid p-heptylphenyl ester, 50 ml of toluene, 50 ml of ethanol and 0.10 g of palladium/barium carbonate catalyst poisoned with 2 wt.% lead was hydrogenated at room temperature until the hydrogen uptake came to a standstill. The mixture was filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel with methylene chloride as the eluent. Recrystallization from methylene chloride/hexane, yielded 0.334 of 1,5-diamino-6-methyl-2-anthraquinonecarboxylic acid p-heptylphenyl ester as violet crystals; m.p. (C-N) 163.7°-165.7° C., cl.p. (N-I) 190.9°-191.4° C., nematic; E277 =15280, E524 =14700.

後処理

  1. filtrationThe mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by chromatography on silica gel with methylene chloride as the eluent
  4. customRecrystallization from methylene chloride/hexane

出典と根拠

ORDレコード
ord-214e9e825054420aa86fb83ded385f06
出典データセット
uspto-grants-1986_09
特許番号
US04613208

反応ノート

読み込み中…