Hydrochloric Acid → 7,8-Diamino-1-hydroxy-3-naphthalene sulfonic acid dihydrochloride

HRID 25313

반응식

HRID 25313 반응식
S([O-])(=O)(C1C=CC([NH2:9])=CC=1)=O.[Na+].N([O-])=O.[Na+].[ClH:17].[NH2:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[C:24]([S:30]([OH:33])(=[O:32])=[O:31])[CH:25]=[C:26]2[OH:29])=[CH:21][CH:20]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[ClH:17].[ClH:17].[NH2:18][C:19]1[C:28]([NH2:9])=[C:27]2[C:22]([CH:23]=[C:24]([S:30]([OH:33])(=[O:31])=[O:32])[CH:25]=[C:26]2[OH:29])=[CH:21][CH:20]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 70222-Amino-8-hydroxynaphthalene-6-sulfonic acidHCID 24489Sodium DithioniteHCID 23664644Sodium sulfanilateHCID 23668193Sodium Nitrite

생성물 1

HCID 878858447,8-Diamino-1-hydroxy-3-naphthalene sulfonic acid dihydrochloride수율 45%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A stirred solution of p-benzenediazonium sulfonic acid, was prepared by the addition of sodium sulfanilate (1.10 g, 5.2 mmole) to sodium nitrite (0.40 g, 5.7 mmole) in water (10 mL) followed by addition to ice (6.0 g) and concentrated HCl (1.1 mL, 37%). After 30 min. of standing at 0° C. 7-amino-1-hydroxy-3-naphthalene sulfonic acid (1.2 g, 5.2 mmole) was added in water (10 mL) and the reaction was stirred at room temperature overnight. The reaction mixture was warmed to 50° C. and sodium hydrosulfite (3.0 g, 15.6 mmole) was added and the reaction was stirred for 4 hours. The reaction was filtered and the precipitate was washed with water, methanol, and ether to give the title compound (0.54 g; 45%) as a red solid. MS(ES) m/z 255 [M+H].

후처리

  1. temperatureThe reaction mixture was warmed to 50° C.
  2. stirringthe reaction was stirred for 4 hours
  3. filtrationThe reaction was filtered
  4. washthe precipitate was washed with water, methanol, and ether

출처 및 근거

ORD 기록
ord-f48772335f1d4b98924d18b5e0cf3276
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858630B2

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