Triethylamine → 5-Methoxy-4-methylindole

HRID 6743

반응식

HRID 6743 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[C:5]([CH3:12])[C:4]=1[CH3:13].[CH3:14]OC(OC)N(C)C.C(N(CC)CC)C>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([CH3:13])=[C:5]2[C:6](=[CH:7][CH:8]=1)[NH:9][CH:14]=[CH:12]2

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 5964652,3-Dimethyl-4-nitroanisole

생성물 1

HCID 32962425-Methoxy-4-methylindole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1-methoxy-2,3-dimethyl-4-nitro-benzene (5.0 g), N,N-dimethylformamide dimethylacetal (7.4 mL) and triethylamine (0.10 mL) in 25 mL of N,N-dimethylformamide was heated to reflux for 3 days under nitrogen. The volatiles were removed in vacuo and the resulting residue was dissolved in 40 mL of a 1:1 mixture of methanol and tetrahydrofuran. Raney nickel (50% slurry in water, 1 mL) was added to the solution, then hydrazine hydrate (2.7 mL) was added dropwise and the mixture was stirred for 40 min under nitrogen. The reaction mixture was filtered through a bed of celite and the filtrate was reduced in vacuo. The product was purified by column chromatography (30% ethyl acetate in hexanes) to yield 1.5 g of pure 5-methoxy-4-methyl-indole.

후처리

  1. temperatureto reflux for 3 days under nitrogen
  2. customThe volatiles were removed in vacuo
  3. dissolutionthe resulting residue was dissolved in 40 mL of a 1:1 mixture of methanol and tetrahydrofuran
  4. additionRaney nickel (50% slurry in water, 1 mL) was added to the solution
  5. additionhydrazine hydrate (2.7 mL) was added dropwise
  6. filtrationThe reaction mixture was filtered through a bed of celite
  7. customThe product was purified by column chromatography (30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-068e324f42144e96b9bab928625a14ad
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084154B2

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