4-Nitroanthranilic acid → Methyl 4-nitroanthranilate

HRID 29659

反応式

HRID 29659 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:13])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9])([O-:3])=[O:2].[Si](C=[N+]=[N-])(C)(C)[CH3:15]>C1C=CC=CC=1.CO>[CH3:15][O:9][C:8](=[O:10])[C:7]1[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)[NH2:13]

参加物

4

反応物 2

HCID 120764-Nitroanthranilic acidHCID 167693Trimethylsilyldiazomethane

生成物 1

HCID 596476Methyl 4-nitroanthranilate収率 86.1%

試薬・触媒・溶媒 1

HCID 21927730Benzene methanol溶媒

実験手順

To a solution of 4-nitro-anthranilic acid (2.200 g, 10.9 mmol, 1 eq) in benzene/methanol (4/1) (100 mL) was added TMSCHN2 (2M in hexanes) (12 mL, 24 mmol, 2.2 eq). The reaction was stirred at room temperature for 30 minutes and then concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80) to afford 4-nitro-anthranilic acid methyl ester (1.841 g, 86%) as a bright yellow solid. 1H NMR (300 MHz, CDCl3); δ 8.00 (d, 1H), 7.50 (d, 1H), 7.40 (dd, 1H), 3.92 (s, 3H).

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-c4c7adf42b564347b9dd32ea4aedb73c
出典データセット
uspto-grants-2008_09
特許番号
US07420083B2

関連ノート

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