Dimethylformamide → HCID 58966768、化合物

HRID 2235168

反応式

HRID 2235168 の反応式
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5](C(O)=O)=[CH:4][C:3]=1[N+:12]([O-])=O.C[O:16][CH:17]([O:21][CH3:22])N(C)C.O.NN.[CH3:26]N(C)C=O>CO.[Ni]>[CH3:22][O:21][C:17]([C:5]1[CH:4]=[C:3]2[C:2]([CH:1]=[CH:26][NH:12]2)=[C:10]([CH3:11])[CH:9]=1)=[O:16]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 113675723,4-Dimethyl-5-nitrobenzoic acid

生成物 1

HCID 58966768HCID 58966768、化合物収率 69%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

実験手順

A solution of 4,5-dimethyl-3-nitrobenzoic acid (Helv. Chim. Acta 1980, 37, 385; 2.50 g, 12.8 mmol) and N,N-dimethylformamide dimethyl acetal (3.66 g, 30.7 mmol) in N,N-dimethylformamide (25 mL) was heated at 140° C. for 4 h, then volatile material was removed by distillation. The residue was taken up in tetrahydrofuran (10 mL) and methanol (10 mL), then Raney nickel (aqueous suspension, 1 mL) and hydrazine hydrate (1.85 g, 57.6 mmol) were added over 30 min in three portions at 50° C., and the reaction was kept at 50° C. for another 90 min. The reaction mixture was filtered through diatomaceous earth, the filtrate was dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate 2:1) produced 4-methyl-1H-indole-6-carboxylic acid methyl ester (1.68 g, 69%). White solid, MS (ISP): m/e 190.3 (M+H).

後処理

  1. customvolatile material was removed by distillation
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. dry with materialthe filtrate was dried (MgSO4)
  4. customevaporated

出典と根拠

ORDレコード
ord-c444d1b4de2c45af81f40bc4ca9dd41e
出典データセット
uspto-grants-2010_05
特許番号
US07713996B2

関連ノート

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