Acetic Acid → 4-(2-amino-4,5-dimethylphenoxymethyl)-3-methylbenzoic Acid Methyl Ester

HRID 1866201노트

반응식

HRID 1866201 반응식
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:13]=2[N+:20]([O-])=O)=[C:6]([CH3:23])[CH:5]=1.C(O)(=O)C>[Fe].O>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:13]=2[NH2:20])=[C:6]([CH3:23])[CH:5]=1

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 588919084-(2-nitro-4,5-dimethylphenoxymethyl)-3-methylbenzoic Acid Methyl Ester

생성물 1

HCID 588919054-(2-amino-4,5-dimethylphenoxymethyl)-3-methylbenzoic Acid Methyl Ester

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

A mixture of 4-(2-nitro-4,5-dimethylphenoxymethyl)-3-methylbenzoic acid methyl ester prepared in Reference Example 1 (7.21 g), acetic acid (88 ml) and water (8.8 ml) was stirred at 50° C. To the reaction solution, iron powder (6.11 g) was gradually added, and the mixture was stirred for 1 hour at 50° C. After cooling, the mixture was filtered and the filtrate was concentrated and azeotroped with toluene. To the residue, ethyl acetate-water (100 ml-100 ml) was added and the mixture was filtrated over Celite (registered trademark). The organic layer was washed, dried, concentrated under reduced pressure to give the title compound (4.66 g) having the following physical data.

후처리

  1. stirringthe mixture was stirred for 1 hour at 50° C
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customazeotroped with toluene
  6. additionTo the residue, ethyl acetate-water (100 ml-100 ml) was added
  7. filtrationthe mixture was filtrated over Celite (registered trademark)
  8. washThe organic layer was washed
  9. customdried
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c507ecb755b542f3a3ddc3822845d926
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629369B2

반응 노트

불러오는 중…