Hydroquinone → 1-Aminoanthraquinone

HRID 973000

반응식

HRID 973000 반응식
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[N+](C1C2C(=O)C3C(=C([N+]([O-])=O)C=CC=3)C(=O)C=2C=CC=1)([O-])=O.[N+](C1C2C(=O)C3C(=CC=CC=3[N+]([O-])=O)C(=O)C=2C=CC=1)([O-])=O.C1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1.[N+](C1C=CC2C(=O)C3C(=CC=CC=3)C(=O)C=2C=1)([O-])=O.[H][H].C1(C=CC(O)=CC=1)O>>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1

참가 물질

8

반응물 7

HCID 785HydroquinoneHCID 67041-Nitroanthraquinone2회HCID 67059,10-Anthracenedione, 1,5-dinitro-HCID 6780AnthraquinoneHCID 672101,8-Dinitro-9,10-anthraquinoneHCID 39285932-NitroanthraquinoneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67101-Aminoanthraquinone수율 72.6%

실험 절차

5.0 g of crude 1-nitroanthraquinone containing dinitroanthraquinones having a purity of 81% and containing 8% of 1,5-dinitroanthraquinone, 4% of 1,8-dinitroanthraquinone and 7% of other dinitroanthraquinones and being free from anthraquinone and 2-nitroanthraquinone (0.016 mole of 1-nitroanthraquinone and 0.0032 mold of all the dinitroanthraquinones) was hydrogenated in the same way as in Example 5. The reaction was stopped when the amount of hydrogen absorbed reached 0.0816 mole, and the inside of the flask was purged with nitrogen. The amount of hydrogen absorbed corresponded to the sum of the amount of hydrogen required to convert the nitro group to an amino group (0.0672 mole) and 90% of the amount of hydrogen required to convert 1-aminoanthraquinone to its hydroquinone derivative (0.0144 mole). The reaction mixture was filtered in a stream of nitrogen to separate the catalyst and insoluble materials from it. The filtrate was oxidized with air at 20° to 30° C. for 2 hours with stirring to afford 3.2 g of 1-aminoanthraquinone having a purity of 98%. The yield of the product was 88% on a purity basis. The resulting 1-aminoanthraquinone contained about 1% of 1,8-diaminoanthraquinone and only traces of other diamino isomers.

후처리

  1. customabsorbed
  2. customthe inside of the flask was purged with nitrogen
  3. customThe amount of hydrogen absorbed
  4. filtrationThe reaction mixture was filtered in a stream of nitrogen
  5. customto separate the catalyst and insoluble materials from it

출처 및 근거

ORD 기록
ord-967d535ca9b3419b8022045db011473e
출처 데이터셋
uspto-grants-1977_10
특허 번호
US04054586

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