Acetic Anhydride → (2-Acetylamino-4-trifluoromethylphenyl)-acetic acid methyl ester

HRID 388623

반응식

HRID 388623 반응식
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[N+:15]([O-])=O.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C1(C)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[NH:15][C:19](=[O:21])[CH3:20]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 83569Methyl 2-(2-nitro-4-(trifluoromethyl)phenyl)acetate

생성물 1

HCID 57633614(2-Acetylamino-4-trifluoromethylphenyl)-acetic acid methyl ester수율 95%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 1140Toluene용매

실험 절차

Hydrogenation and acetylation of (2-nitro-4-trifluoromethylphenyl)-acetic acid methyl ester (25 g, 0.095 mol) in the presence of 5% Pd—C (2.5 g, 50% wet) and acetic anhydride (38 g, 0.37 mol) in toluene (200 mL) was carried out under vigorous stirring at room temperature and atmospheric pressure for about 4-5 h (reaction monitored by TLC). The catalyst was removed by filtration and washed with toluene two times. The combined organics were evaporated in vacuo to yield the product (24.8 g, 95%), which was used without further purification in the next step. A small sample was crystallized from hexane to yield the product as a yellow solid, mp 92-94° C. 1H NMR (CDCl3) 8.86 (s, 1H), 8.21 (s, 1H), 7.36 (d, J=8.1 Hz, 1H), 7.31 (d, J=8.1 Hz, 1H), 3.74 (s, 3H), 3.68 (s, 2H), 2.23 (s, 3H).

후처리

  1. customatmospheric pressure for about 4-5 h (reaction monitored by TLC)
  2. customThe catalyst was removed by filtration
  3. washwashed with toluene two times
  4. customThe combined organics were evaporated in vacuo

출처 및 근거

ORD 기록
ord-f722ed5d70644a3bb69bd32ce48c36e5
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377958B2

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