Dimethylformamide → N-(1,3-Dimethyl-5-pyrazolyl)anthranilic acid

HRID 977136

反応式

HRID 977136 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]([CH3:17])[N:15]=[C:14]([CH3:18])[CH:13]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C>[CH3:17][N:16]1[C:12]([NH:11][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:13][C:14]([CH3:18])=[N:15]1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

生成物 1

HCID 615796N-(1,3-Dimethyl-5-pyrazolyl)anthranilic acid収率 44.7%

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 (14.9 g, 0.06 mol), 5-amino-1,3-dimethylpyrazole (6.7 g, 0.06 mol), DMF (125 ml), Cu(OAc)2 (0,4 g) and K2CO3 (8.28 g, 0.06 mol) was refluxed overnight. The reaction mixture was poured into ice-water (500 ml) and then was acidified with acetic acid to a pH of about 5. The solid which formed was collected by filtration, washed with water (100 ml) and dried. The solid was dissolved in hot CHCl3 (300 ml), filtered, dried over MgSO4 and evaporated to about 20 ml. Hexane (50 ml) was added and then the product was collected by filtration, washed with hexane (30 ml) and dried to afford 6.2 g of N-(1,3-dimethyl-pyrazol-5-yl)anthranilic acid, m.p. 210°-211° C.

後処理

  1. temperaturewas refluxed overnight
  2. customThe solid which formed
  3. filtrationwas collected by filtration
  4. washwashed with water (100 ml)
  5. customdried
  6. dissolutionThe solid was dissolved in hot CHCl3 (300 ml)
  7. filtrationfiltered
  8. dry with materialdried over MgSO4
  9. customevaporated to about 20 ml
  10. additionHexane (50 ml) was added
  11. filtrationthe product was collected by filtration
  12. washwashed with hexane (30 ml)
  13. customdried

出典と根拠

ORDレコード
ord-9c9551a600524f88842724108d416682
出典データセット
uspto-grants-1997_03
特許番号
US05614530

関連ノート

読み込み中…