Methyl iodide → Methyl 2-methyl-4-(methylamino)-3-nitrobenzoate

HRID 906129ノート

反応式

HRID 906129 の反応式
I[CH3:2].[NH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:14])[C:5]=1[N+:15]([O-:17])=[O:16].[H-].[Na+]>O1CCCC1>[CH3:14][C:6]1[C:5]([N+:15]([O-:17])=[O:16])=[C:4]([NH:3][CH3:2])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67404328HCID 67404328、化合物

生成物 1

HCID 67403462Methyl 2-methyl-4-(methylamino)-3-nitrobenzoate収率 72.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Iodomethane (125 uL, 2.0 mmol) was added to a mixture of the methyl 4-amino-2-methyl-3-nitrobenzoate (400 mg, 1.9 mmol) and sodium hydride (60% oil dispersion, 84 mg, 2.1 mmol) in tetrahydrofuran (10 mL) at 0° C. The reaction mixture was slowly warmed to room temperature and stirred for 18 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined extract was washed with water (2×30 mL), brine (30 mL), dried over sodium sulfate, filtered and concentrated, then purified by flash chromatography (25% ethyl acetate in hexanes) to give methyl 2-methyl-4-(methylamino)-3-nitrobenzoate (308 mg, 72% yield). 1H NMR (400 MHz, CDCl3): 7.94 (d, 1H), 6.63 (d, 1H), 5.68 (br, 1H), 3.86 (d, 2H), 2.58 (s, 3H); MS (EI) for C10H12N2O4: 225 (MH+).

後処理

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with water (2×30 mL), brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography (25% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-c96b4f8d9d74455e93f6c16fffb51a11
出典データセット
uspto-grants-2011_09
特許番号
US08012956B2

反応ノート

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