Indole → 5-Methoxyindole

HRID 355095

반응식

HRID 355095 반응식
C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.N1C2C(=CC=CC=2)CC1.[H][H].N1C2C(=CC=CC=2)C=C1.[CH3:33][O:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][CH2:39][CH2:38]2.C1(C)C=C(C)C=C(C)C=1>[Ni].[Pd].[Pt]>[CH3:33][O:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][CH:39]=[CH:38]2

참가 물질

10

반응물 6

HCID 798IndoleHCID 7947MesityleneHCID 8371ChloranilHCID 10328Indoline2회HCID 107019745-methoxy-2,3-dihydro-1H-indoleHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 138725-Methoxyindole수율 90%

시약·촉매·용매 3

HCID 935Nickel촉매HCID 23938Palladium촉매2회HCID 23939Platinum촉매

실험 절차

Ikan et al. [Israel J. of Chemistry, Vol. 2 (1964), p. 37-42] and Terent'ev et al. [Proc. Acad. Sci. USSR, Vol. 118 (2) (1958), p. 49-52] describe the dehydration of 5-chloro-indoline with chloranil to obtain 5-chloro-indole but due to the expense of chloranil, the process is not commercially feasible. French Pat. No. 1,576,807, DOS No. 1,770,977, Chem. Abs., Vol. 72 (1970), p. 121360n and Bader et al. [J.A.C.S., Vol. 83 (1961), p. 3319] tried to avoid this difficulty with partial success by heating indoline and its derivatives to high temperatures in the presence of palladium, platinum of Raney nickel catalysts, sometimes in the presence of a hydrogen acceptor. For example, indoline can be dehydrated at 100 to 150° C. in aromatics with a good yield of indole with hydrogen in the presence of finely divided palladium. Hunt et al. [J. Chem. Soc., (C) (1966), p. 344-345] teach reacting 5-methoxy-indoline in refluxing mesitylene in the presence of palladized carbon to obtain a 90% yield of 5-methoxy-indole.

출처 및 근거

ORD 기록
ord-794e16b03079497390202f6bfd322d32
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04377699

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