4-Ethylbenzoic Acid → Methyl 3-methyl-1H-indole-6-carboxylate

HRID 1242135노트

반응식

HRID 1242135 반응식
[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:13]([O-])=O)[CH3:2].[CH2:16](C1C=CC(C(O)=O)=CC=1)C.COC(OC)N(C)C>CN(C)C=O>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[C:4]2[C:3]([C:1]([CH3:16])=[CH:2][NH:13]2)=[CH:12][CH:11]=1)=[O:8]

참가 물질

5

반응물 3

HCID 120864-Ethylbenzoic AcidHCID 78373Dimethylformamide dimethyl acetalHCID 21938352Methyl 4-ethyl-3-nitrobenzoate

생성물 1

HCID 21938240Methyl 3-methyl-1H-indole-6-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

Methyl 4-ethyl-3-nitrobenzoate (5.0 g), which had been prepared through nitration followed by methyl-esterification of 4-ethylbenzoic acid, is dissolved in N,N-dimethylformamide (50 ml), to which is added N,N-dimethylformamide dimethyl acetal (8.45 g), and stirred under heat at 130° C. for 3 hours. The reaction mixture is concentrated under reduced pressure, and the resulting red oily residue is dissolved in methanol (50 ml), to which is added palladium-carbon (5%, 0.400 g), and stirred in a hydrogen atmosphere at room temperature for 2.5 hours. Then, this is further stirred at 50° C. for 2 hours and thereafter at room temperature for 3 days. The catalyst is removed through filtration, and the filtrate is concentrated under reduced pressure. The resulting residue is recrystallized from t-butyl methyl ether to obtain a pale yellow crystal of the intended product (2.4 g).

후처리

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutionthe resulting red oily residue is dissolved in methanol (50 ml), to which
  3. additionis added palladium-carbon (5%, 0.400 g)
  4. stirringstirred in a hydrogen atmosphere at room temperature for 2.5 hours
  5. stirringThen, this is further stirred at 50° C. for 2 hours
  6. customThe catalyst is removed through filtration
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe resulting residue is recrystallized from t-butyl methyl ether

출처 및 근거

ORD 기록
ord-356be7b1a1e84db4bfec2619f722bea0
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115647B2

반응 노트

불러오는 중…