Hydrochloric Acid → 1-Hydroxynaphthalene-7-sulfonic acid

HRID 528801

反応式

HRID 528801 の反応式
N[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([OH:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2.[OH:16]S([O-])=O.[Na+].[OH-].[Na+].Cl>O>[OH:16][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([OH:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8386Cleve's acidHCID 14798Sodium HydroxideHCID 23665763Sodium Bisulfite

生成物 1

HCID 30224821-Hydroxynaphthalene-7-sulfonic acid収率 99.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 8-amino-2-naphthalenesulfonic acid (Aldrich, 2.40 g, 10.8 mmol) and 3.9M aq. NaHSO3 solution (20.0 mL, 77.0 mmol) in water (10.0 mL) was refluxed for 15 h. The reaction mixture was then basified with 30% aq. NaOH solution (430 mg, 10.8 mmol) and refluxed for 4 h. The reaction mixture was neutralized with conc. HCl and then concentrated in vacuo. The remaining solid was azeotroped with 1:1 MeOH/PhMe (3×) to give the title compound (2.41 g, 95%). 1H NMR (DMSO-d6) δ 9.43 (br s, 1H), 8.36 (s, 1H), 7.96 d, J=8.4 Hz, 1H), 7.88-7.78 (m, 2H), 7.52 (t, J=7.8 Hz, 1H), 7.43 (d, J=7.3 Hz, 1H); MS(ESI−) m/z 222.3 (M−H)−.

後処理

  1. temperaturerefluxed for 4 h
  2. concentrationconcentrated in vacuo
  3. customThe remaining solid was azeotroped with 1:1 MeOH/PhMe (3×)

出典と根拠

ORDレコード
ord-38d8d658b8c0402f91d2326e7952801e
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

関連ノート

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