Dimethylformamide → N-(1-cyclopentylpyrazol-5-yl) anthranilic acid

HRID 375860

반응식

HRID 375860 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.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>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

6

반응물 4

HCID 6228DimethylformamideHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 10797921-cyclopentyl-1H-pyrazol-5-amine

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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

후처리

  1. temperaturewas refluxed overnight
  2. customThe gum which formed
  3. extractionwas extracted with CH2Cl2
  4. washthe CH2Cl2 layer was washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated

출처 및 근거

ORD 기록
ord-24c745ae42994c5db88ebabca4b6f325
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488055

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