Methyl iodide → Methyl 2-amino-5-(propan-2-yloxy)benzoate

HRID 1070401ノート

反応式

HRID 1070401 の反応式
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])([CH3:3])[CH3:2].[H-].[Na+].[CH3:17]I.OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C>[CH3:17][O:11][C:10](=[O:12])[C:9]1[CH:13]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:6]=[CH:7][C:8]=1[NH2:14]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 127191892-Amino-5-(propan-2-yloxy)benzoic acidHCID 86586342KHSO4 Na2SO4

生成物 1

HCID 13052308Methyl 2-amino-5-(propan-2-yloxy)benzoate収率 13.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-isopropoxy-2-amino-benzoic acid (806 mg) in DMF (10 mL) was added 60% in oil NaH (182 mg, 4.53 mmol) at 0-5° C. under an argon atmosphere. The ice bath was removed and the mixture was stirred for 40 min at room temperature. After addition of methyl iodide (0.33 mL, 5.45 mmol) the mixture was stirred at room temperature for an additional 6 h. 10% KHSO4/Na2SO4 was added and the mixture was extracted, washed with brine, dried (Na2SO4), and concentrated to dryness. Purification by chromatography gave 114 mg of 5-isopropoxy-2-amino-benzoic acid methyl ester.

後処理

  1. customThe ice bath was removed
  2. stirringwas stirred at room temperature for an additional 6 h
  3. extractionthe mixture was extracted
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customPurification by chromatography

出典と根拠

ORDレコード
ord-c77e9a02071f455a8348f80f04503007
出典データセット
uspto-grants-2005_06
特許番号
US06903086B2

反応ノート

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