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

HRID 1586144

반응식

HRID 1586144 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5e2f2f46e0224fa4aface44e342bd7da
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05942520

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