Acetic Acid → 2-Amino-5-(methoxycarbonyl)benzoic acid

HRID 2110035

反応式

HRID 2110035 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:8](I)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CCN(CC)CC.[CH:19]1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C]=O.[C:50]([OH:53])(=[O:52])C>CN(C=O)C.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:50]([O:53][CH3:19])=[O:52])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

参加物

10

反応物 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 812191,3-Bis(diphenylphosphino)propaneHCID 178418416HCID 178418416、化合物

生成物 1

HCID 131050362-Amino-5-(methoxycarbonyl)benzoic acid

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

After dissolving 2-amino-5-iodobenzoic acid (4 mmol, 1052 mg) in DMF (10 ml) and MeOH (5 ml), NEt3 (3 eq, 1.67 ml) was added. Next, palladium acetate (0.1 eq, 90 mg) and dppp (0.1 eq, 165 mg) were added, carbon monoxide substitution was carried out, and the mixture was stirred at 80° C. for 5 hours. Upon completion of the reaction, acetic acid (2.5 ml) was added to suspend the reaction. Water (50 ml) was added, and extraction was performed with ethyl acetate (50 ml×3 times). The organic layer was washed with water (100 ml×2 times) and then dried over sodium sulfate. After concentration, a developing solvent (Hex/AcOEt=4/1→1/1) was used for purification by silica gel chromatography to obtain 2-amino-5-(methoxycarbonyl)benzoic acid. The compound was identified by LC-MS.

後処理

  1. additionwas added
  2. additionwas added
  3. customthe reaction
  4. extractionextraction
  5. washThe organic layer was washed with water (100 ml×2 times)
  6. dry with materialdried over sodium sulfate
  7. concentrationAfter concentration
  8. customa developing solvent (Hex/AcOEt=4/1→1/1) was used for purification by silica gel chromatography

出典と根拠

ORDレコード
ord-048688c5d3694dddb090ba85c4bb8d4f
出典データセット
uspto-grants-2009_04
特許番号
US07517875B2

関連ノート

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