Hydrochloric Acid → 2-Iodo-4-methoxybenzoic acid

HRID 613270

반응식

HRID 613270 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5](N)[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8].Cl.N([O-])=O.[Na+].[I-:18].[K+].OS(O)(=O)=O.II>O.C1(C)C=CC=CC=1>[I:18][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 3510102-Amino-4-methoxybenzoic acidHCID 23668193Sodium Nitrite

생성물 1

HCID 128221822-Iodo-4-methoxybenzoic acid수율 52%

시약·촉매·용매 2

HCID 962Water용매3회HCID 1140Toluene용매

반응 조건

온도
75 °C

실험 절차

A mixture of 4-methoxyanthranilic acid (30.5 g, 0.18 mol), water (274.5 ml), and concentrated HCl (36.6 ml) was heated at 75° C. to effect solution and then was cooled to 0° C. The mixture was then treated with NaNO2 (13.3 g) in water (27.5 ml), followed by potassium iodide (45.75 g) in a water (75 ml)/H2SO4 (10.1 ml) solution. The reaction mixture was heated on a steam bath for 2 hours, then excess iodine was steam distilled. The reaction mixture was then cooled and the product was collected by filtration and dried in an oven at 75° C. To afford 39.28 g (78.6%) of crude product. The crude product was treated with toluene, the mixture was filtered and the filtrate was concentrated to afford 26.03 g of 2-iodo-4-methoxybenzoic acid.

후처리

  1. temperaturewas cooled to 0° C
  2. temperatureThe reaction mixture was heated on a steam bath for 2 hours
  3. distillationdistilled
  4. temperatureThe reaction mixture was then cooled
  5. filtrationthe product was collected by filtration
  6. customdried in an oven at 75° C
  7. customTo afford 39.28 g (78.6%) of crude product
  8. filtrationthe mixture was filtered
  9. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-593e53600721465ca80007ad82b445f8
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008226

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