2-Iodobenzoic acid → N-(1-cyclopentylpyrazol-5-yl) anthranilic acid

HRID 1586144

反応式

HRID 1586144 の反応式
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:11][C:12]1[N:16]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:15]=[CH:14][CH:13]=1.COCCOC.C(=O)([O-])[O-].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C>[CH:17]1([N:16]2[C:12]([NH:11][C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]([OH:6])=[O:5])=[CH:13][CH:14]=[N:15]2)[CH2:18][CH2:19][CH2:20][CH2:21]1

参加物

7

反応物 4

HCID 69412-Iodobenzoic acidHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 10797921-cyclopentyl-1H-pyrazol-5-amine

生成物 1

HCID 54038843N-(1-cyclopentylpyrazol-5-yl) anthranilic acid収率 68.5%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 176Acetic Acid溶媒

実験手順

A mixture of 2-iodobenzoic acid (28 g, 0.113 mol), 5-amino-1-cyclopentylpyrazole (17 g, 0.113 mol), DME (100 ml), potassium carbonate (16 g, 0.113 mol) and Cu(OAc)2 (0.5 g) is refluxed overnight. The reaction mixture is poured into ice water, and acidified with acetic acid to a pH of 5. The gum which forms is extracted with CH2Cl2 and the CH2Cl2 layer is washed with water, dried over MgSO4, and evaporated to afford 21 g of N-(1-cyclopentyl pyrazol-5-yl) anthranilic acid.

後処理

  1. temperatureis refluxed overnight
  2. extractionThe gum which forms is extracted with CH2Cl2
  3. washthe CH2Cl2 layer is washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated

出典と根拠

ORDレコード
ord-5e2f2f46e0224fa4aface44e342bd7da
出典データセット
uspto-grants-1999_08
特許番号
US05942520

関連ノート

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