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

HRID 65177노트

반응식

HRID 65177 반응식
[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]

참가 물질

6

반응물 3

HCID 1140TolueneHCID 54519986HCID 54519986, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-214e9e825054420aa86fb83ded385f06
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04613208

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