Naphthalic anhydride → 8-(6-Ethylamino-3-ethylimino-2,7-dimethyl-3H-xanthen-9-yl)naphthalene-carboxylic acid

HRID 10077

반응식

HRID 10077 반응식
[CH2:1]([NH:3][C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[CH:8][C:9]=1[CH3:10])[CH3:2].[C:12]1(=O)[C:21]2[C:16]3[C:17](=[CH:22][CH:23]=[CH:24][C:15]=3[C:14](=[O:25])[O:13]1)[CH:18]=[CH:19][CH:20]=2>S(=O)(=O)(O)O>[CH2:1]([NH:3][C:4]1[CH:5]=[C:6]2[C:7](=[CH:8][C:9]=1[CH3:10])[C:12]([C:21]1[CH:20]=[CH:19][CH:18]=[C:17]3[C:16]=1[C:15]([C:14]([OH:13])=[O:25])=[CH:24][CH:23]=[CH:22]3)=[C:7]1[C:6](=[CH:5][C:4](=[N:3][CH2:1][CH3:2])[C:9]([CH3:10])=[CH:8]1)[O:11]2)[CH3:2]

참가 물질

4

반응물 2

HCID 6693Naphthalic anhydrideHCID 84283-Ethylamino-4-methylphenol

생성물 1

HCID 219883828-(6-Ethylamino-3-ethylimino-2,7-dimethyl-3H-xanthen-9-yl)naphthalene-carboxylic acid수율 10.8%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

3-Ethylamino-4-methyl-phenol (0.3 g, 2 mmol) and benzo[de]isochromene-1,3-dione (0.2 g, 1 mmol) in sulfuric acid (3 ml) was heated to 150° C. over a period of 6 h. The reaction mixture was pouring into crushed ice, allowed to stand over a period of 1 h and the precipitate was filtered. The filtrate was neutralized with concentrated ammonium hydroxide and concentrated to give a dark purple residue. Purification via preparatory layer chromatography (PLC, 1 mm silica gel, 9/1 DCM: MeOH, 2% AcOH) gave the title compound (50 mg). ABS λmax=527 nm (EtOH).

후처리

  1. additionThe reaction mixture was pouring
  2. custominto crushed ice
  3. filtrationthe precipitate was filtered
  4. concentrationconcentrated
  5. customto give a dark purple residue
  6. customPurification via preparatory layer chromatography (PLC, 1 mm silica gel, 9/1 DCM: MeOH, 2% AcOH)

출처 및 근거

ORD 기록
ord-d406d35cc3c140e4a123a0c440055f56
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091348B2

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