Hydrochloric Acid → 3-Hydroxy-4-iodonaphthalene-2-carboxylic acid

HRID 1062947노트

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HRID 1062947 반응식
[OH-].[Na+].[I-:3].[Na+].[OH:5][C:6]1[C:7]([C:16]([OH:18])=[O:17])=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.Cl[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>CO>[OH:5][C:6]1[C:7]([C:16]([OH:18])=[O:17])=[CH:8][C:9]2[C:14]([C:15]=1[I:3])=[CH:13][CH:12]=[CH:11][CH:10]=2

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 71043-Hydroxy-2-naphthoic acidHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 23665760Sodium Hypochlorite

생성물 1

HCID 2422513-Hydroxy-4-iodonaphthalene-2-carboxylic acid수율 75.1%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

A mixture of NaOH (2.12 g) in methanol (100 mL) was stirred until the solution was homogeneous. Sodium iodide (3.98 g) and 3-hydroxy-2-naphthoic acid (5.00 g) were added and allowed to stir for 30 min. The resulting suspension was cooled to 0° C. and a 5.25% (w/v) aqueous solution of sodium hypochlorite was added dropwise and stirring continued for 1 h. Saturated sodium thiosulfate (25 mL) was added and after 5 min the solution was acidified to pH 2 by addition of 6 N HCl resulting in the formation of a yellow precipitate which was filtered and washed with water (50 mL). The precipitate was transferred to a round-bottomed flask, dissolved in methanol (70 mL) and toluene (100 mL), concentrated, redissolved in methanol (70 mL), concentrated, redissolved again in methanol (70 mL) and toluene (100 mL) and concentrated to afford the product as a yellow solid (6.26 g). MS m/z 313 (M−1). 1H NMR (DMSO-d6): δ 12.41 (broad, 1 H), 8.63 (s, 1 H), 8.05-7.97 (m, 2 H), 7.70 (m, 1 H), 7.42 (m, 1H).

후처리

  1. stirringto stir for 30 min
  2. stirringstirring
  3. filtrationwas filtered
  4. washwashed with water (50 mL)
  5. customThe precipitate was transferred to a round-bottomed flask
  6. dissolutiondissolved in methanol (70 mL)
  7. concentrationtoluene (100 mL), concentrated
  8. dissolutionredissolved in methanol (70 mL)
  9. concentrationconcentrated
  10. dissolutionredissolved again in methanol (70 mL)
  11. concentrationtoluene (100 mL) and concentrated

출처 및 근거

ORD 기록
ord-5c53cca19ab44ba695ec5bc8708d874e
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06963011B2

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