Hydrochloric Acid → methyl 4-iodo-1H-indole-6-carboxylate

HRID 348967

反応式

HRID 348967 の反応式
N[C:2]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.Cl.N([O-])=O.[Na+].[I-:20].[Na+]>O>[I:20][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 14243967Methyl 4-amino-1H-indole-6-carboxylateHCID 23668193Sodium Nitrite

生成物 1

HCID 851585methyl 4-iodo-1H-indole-6-carboxylate収率 16.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

実験手順

To a mixture of methyl 4-amino-1H-indole-6-carboxylate (EXAMPLE SP-216, step 3) (3.2 g) in water (50 mL) was added concentrated hydrochloric acid (5 mL). The mixture was chilled to below 5° C. with the addition of ice. To this was added sodium nitrite (1.16 g) dissolved in water (10 mL). The mixture was stirred chilled for 1 h followed by addition of sodium iodide (3 g) in water (20 mL). The mixture was stirred for 30 minutes, filtered and the solids collected by filtration were washed with water and dried at 50° C. The solids turned black and gas evolved rapidly upon drying. Column chromatography on silica gel (200 mL) using 20% hexanes in CH2Cl2 as eluent to give 0.82 g of the title compound: 1H NMR (CDCl3) δ 3.94, 6.55, 7.43, 8.14, 8.22, 8.62.

後処理

  1. temperatureThe mixture was chilled to below 5° C. with the addition of ice
  2. temperaturechilled for 1 h
  3. stirringThe mixture was stirred for 30 minutes
  4. filtrationfiltered
  5. filtrationthe solids collected by filtration
  6. washwere washed with water
  7. customdried at 50° C
  8. customupon drying

出典と根拠

ORDレコード
ord-92cdf23bb052446983ba38eda7dda591
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

関連ノート

読み込み中…