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

HRID 25313

反応式

HRID 25313 の反応式
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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-f48772335f1d4b98924d18b5e0cf3276
出典データセット
uspto-grants-2005_02
特許番号
US06858630B2

関連ノート

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