4-Nitroanthranilic acid → Methyl 4-nitroanthranilate

HRID 29659

반응식

HRID 29659 반응식
[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]

참가 물질

4

반응물 2

HCID 120764-Nitroanthranilic acidHCID 167693Trimethylsilyldiazomethane

생성물 1

HCID 596476Methyl 4-nitroanthranilate수율 86.1%

시약·촉매·용매 1

HCID 21927730Benzene methanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-c4c7adf42b564347b9dd32ea4aedb73c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420083B2

연결된 노트

불러오는 중…