Dimethylformamide → N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid

HRID 613288노트

반응식

HRID 613288 반응식
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:13][C:14]1[N:18]([CH2:19][CH3:20])[N:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:19]([N:18]1[C:14]([NH:13][C:2]2[C:3](=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:15][CH:16]=[N:17]1)[CH3:20]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 899062-Bromo-5-methoxybenzoic acidHCID 3373101-Ethyl-1H-pyrazol-5-amine

생성물 1

HCID 19592240N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid수율 69%

시약·촉매·용매 3

HCID 8895Cupric acetate촉매HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

A mixture of 2-bromo-5-methoxybenzoic acid (141.5 g, 0.61 mol), 5-amino-1-ethylpyrazole (68 g, 0.61 mol), K2CO3 (84.2 g, 0.61 mol), DMF (500 mL) and Cu(OAc)2 (3 g) was refluxed for about 2 days. The reaction mixture was cooled and then was poured into water (1500 mL). The mixture was acidified with acetic acid and the resulting solid was collected by filtration and dried to afford 110 g of N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid.

후처리

  1. temperaturewas refluxed for about 2 days
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe resulting solid was collected by filtration
  4. customdried

출처 및 근거

ORD 기록
ord-4473a5e2474c4370bf2094bd0ade90b9
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008226

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