(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate → Methyl indole-6-carboxylate

HRID 330135

반응식

HRID 330135 반응식
CN(C)/[CH:3]=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-])=O>O1CCCC1.[Pd]>[NH:15]1[C:6]2[C:5](=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]=2)[CH:4]=[CH:3]1

참가 물질

4

반응물 1

HCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

생성물 1

HCID 639844Methyl indole-6-carboxylate수율 85%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (5.58 g) in tetrahydrofuran (100 ml) was hydrogenated at 3.45 bar in the presence of 10% (w/w) palladium on carbon (1.1 g) for 35 min. The catalyst was removed by filtration through diatomaceous earth and the filtrate was evaporated. The residue was dissolved in ethyl acetate and the solution obtained was washed successively with 10% (v/v) hydrochloric acid, water, and brine; then dried (MgSO4) and evaporated to give methyl indole-6-carboxylate (3.32 g, 85%) as a white solid; NMR (80 MHz, CDCl3): 3.92(s, 3H, OCH3), 6.57(m, 1H, H3 -indole), 7.32(t, 1H, H2 -indole), 7.10(d, 1H, H4 -indole), 7.87(dd, 1H, H5 -indole), 8.16(broad s, 1H, H7 -indole).

후처리

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. customthe solution obtained
  5. washwas washed successively with 10% (v/v) hydrochloric acid, water, and brine
  6. dry with materialthen dried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-c851ade32e1545e3b774a6e2b945221d
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04894386

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