Trimethylsilyldiazomethane → HCID 67083635, 화합물

HRID 79006노트

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HRID 79006 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[C:3]=1[CH3:12].[CH3:13][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO>[CH3:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[C:3]([CH3:12])[C:4]=1[Cl:11]

참가 물질

5

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 534306514-Amino-2-chloro-3-methylbenzoic acid

생성물 1

HCID 67083635HCID 67083635, 화합물수율 96%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

To a suspension of 4-amino-2-chloro-3-methyl-benzoic acid (0.64 g, 3.45 mmol) in toluene (10 mL) and methanol (10 mL) at 0° C. was added drop-wise trimethylsilyldiazomethane (3.45 mL, 2 M in hexane, 6.90 mmol). The reaction mixture was stirred at 0° C. for 30 min during which the reagents dissolved. The reaction mixture was quenched by the addition of acetic acid (1 mL) then washed with aqueous saturated sodium bicarbonate solution (10 mL) and the aqueous fraction extracted twice with ethyl acetate (2×10 mL). The combined organic extracts were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a beige solid (0.66 g, 96%). 1H NMR (CDCl3, 400 MHz) 2.26 (3H, s), 3.86 (3H, s), 6.55 (1H, d, J=8.8 Hz), 7.60 (1H, d, J=8.8 Hz).

후처리

  1. dissolutiondissolved
  2. customThe reaction mixture was quenched by the addition of acetic acid (1 mL)
  3. washthen washed with aqueous saturated sodium bicarbonate solution (10 mL)
  4. extractionthe aqueous fraction extracted twice with ethyl acetate (2×10 mL)
  5. washThe combined organic extracts were washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7f7a80a5505b4ab7a3cff63c42703a42
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841462B2

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