Dimethylformamide → Methyl 2-methyl-3-nitrobenzoate

HRID 11747

반응식

HRID 11747 반응식
CN([CH:4]=[O:5])C.[CH3:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](O)=[O:10].IC>O>[CH3:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O:5][CH3:4])=[O:10]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 160962-Methyl-3-nitrobenzoic acid

생성물 1

HCID 601165Methyl 2-methyl-3-nitrobenzoate수율 100%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

With reference to FIG. 4, DMF (130 mL) was added to a well mixed 2-methyl-3-nitrobenzoic acid 2 (50 g, 0.28 mol) and KHCO3 (84 g, 0.84 mol) solution. Since the mixture became highly viscous, it was heated to 40° C. with manual shaking. Iodomethane (79 g, 0.56 mol) was added via syringe after the gas evolution had ceased. The resulting orange colored solution was stirred for 12 hours at room temperature. The reaction mixture was poured into water (800 mL), and the resulting precipitate collected by filtration and dried over P2O5 to give pure methyl 2-methyl-3-nitrobenzoate 3 (56 g, 100%) as a white solid: mp. 64.2–65.5° C.; 1H-NMR (CDCl3) δ 8.00 (d, J=7.8 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.39 (t, J=8.0 Hz, 1H), 3.95 (s, 3H), 2.63 (s, 3H); IR (KBr, cm−1) 1724, 1548, 1279; MS (EI): 195 (M+).

후처리

  1. filtrationthe resulting precipitate collected by filtration
  2. dry with materialdried over P2O5

출처 및 근거

ORD 기록
ord-137b808493674b5286db3185603fd708
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098307B2

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