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Hydrochloric Acid → 4-Amino-3,6-dihydroxy-1-naphthalenesulfonic acid

HRID 1613117
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HRID 1613117 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[C:3]=1[N:13]=O.[S:15]([O-:18])([OH:17])=[O:16].[Na+].S(=O)(O)[O-].Cl>O>[OH:1][C:2]1[CH:11]=[C:10]([S:15]([OH:18])(=[O:17])=[O:16])[C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[C:3]=1[NH2:13]
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 104748BisulfiteHCID 13750455HCID 13750455, 화합물HCID 23665763Sodium Bisulfite

생성물 1

HCID 150551094-Amino-3,6-dihydroxy-1-naphthalenesulfonic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

In the second reaction stage, the 2,7-dihydroxy-1-nitrosonaphthalene (I) which is generally still moist with water and which reacts in the tautomeric oxime form (Ia), is first suspended, according to Boninger, Chem. Ber. 27, 3050 (1894), in commercially-available 37% aqueous sodium hydrogen sulfite solution and stirred at about 20°-25° C. until it is completely dissolved. The bisulfite addition compound (IIa) thus formed is not isolated, but the brown reaction solution is acidified with hydrochloric acid and heated to about 25°-60° C. 2,7-Dihydroxy-1-aminonaphthalene-4-sulfonic acid (II) is formed by reduction of the nitroso group and aromatization of the cycloaliphatic ring system. The aminonaphtholsulfonic acid (II) is isolated by filtering off the resulting light-gray crystals with suction, washing these on a suction filter first with water and then with methanol and, if desired, drying them. The reaction product thus prepared is used without further purification, if appropriate still moist, for the next reaction stage. The yield of reaction product II is about 90-95% of theory. ##STR6##

후처리

  1. customIn the second reaction stage
  2. dissolutionis completely dissolved
  3. customthus formed
  4. customis not isolated
  5. temperatureheated to about 25°-60° C

출처 및 근거

ORD 기록
ord-ec1c22300f1a438599e3759fa930f390
출처 데이터셋
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05192640

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