Dimethylformamide → Methyl 2-methyl-3-nitrobenzoate

HRID 11747

反応式

HRID 11747 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 601165Methyl 2-methyl-3-nitrobenzoate収率 100%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-137b808493674b5286db3185603fd708
出典データセット
uspto-grants-2006_08
特許番号
US07098307B2

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