P-Anisidine → 6-Chloro-2-(4-methoxyanilino)-3-nitrobenzoic acid

HRID 280250

반응식

HRID 280250 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.Cl[C:11]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]([Cl:23])[C:12]=1[C:13]([OH:15])=[O:14]>>[Cl:23][C:16]1[C:12]([C:13]([OH:15])=[O:14])=[C:11]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=1

참가 물질

3

반응물 2

HCID 7732P-AnisidineHCID 3506232,6-Dichloro-3-nitrobenzoic acid

생성물 1

HCID 27780126-Chloro-2-(4-methoxyanilino)-3-nitrobenzoic acid

실험 절차

To 74 g (0.60 mol) of p-anisidine, stirred mechanically at 75 degrees, was added 35.4 g (0.15 mol) of 2,6-dichloro-3-nitrobenzoic acid [Lehmstedt and Schrader, Berichte 70B, 1526 (1937)]in small portions over one-half hour. The mixture was heated at 75 degrees for 24 hours, with stirring during the first two hours. The reaction mixture was cooled, the solid mass shattered, and triturated in a mechanical blender with 300 ml of 2.4N hydrochloric acid. The solid was collected, washed with 3N hydrochloric acid, stirred in 400 ml of 0.5N sodium carbonate, and filtered. The filtrate, diluted with 250 ml of water, was gradually acidified with 4N hydrochloric acid. The precipitate was collected, washed with water, and dried to 38.5 g (79%) of the red title compound, mp 205-213 degrees. A purified sample, from toluene, melts at 212-215 degrees.

후처리

  1. temperatureThe mixture was heated at 75 degrees for 24 hours
  2. temperatureThe reaction mixture was cooled
  3. customtriturated in a mechanical blender with 300 ml of 2.4N hydrochloric acid
  4. customThe solid was collected
  5. washwashed with 3N hydrochloric acid
  6. stirringstirred in 400 ml of 0.5N sodium carbonate
  7. filtrationfiltered
  8. additionThe filtrate, diluted with 250 ml of water
  9. customThe precipitate was collected
  10. washwashed with water
  11. dry with materialdried to 38.5 g (79%) of the red title compound, mp 205-213 degrees

출처 및 근거

ORD 기록
ord-0167cc214a8147138fc621d21f7a3ecc
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588730

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