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

HRID 1242135ノート

反応式

HRID 1242135 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-356be7b1a1e84db4bfec2619f722bea0
出典データセット
uspto-grants-2006_10
特許番号
US07115647B2

反応ノート

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