Ammonia → 5-methyl-1H-indole-2-carboxamide

HRID 1505652

反応式

HRID 1505652 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.S(Cl)(Cl)=O.C(Cl)(Cl)Cl.[NH3:22]>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:22])=[O:13])=[CH:5]2

参加物

6

反応物 4

HCID 222AmmoniaHCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 2591885-methyl-1H-indole-2-carboxylic acid

生成物 1

HCID 47776705-methyl-1H-indole-2-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 0.5 g of 5-methylindole-2-carboxylic acid, 0.25 mL of thionyl chloride, 5 mL of chloroform and small drop of DMF was refluxed for 2 hs. The reaction mixture was cooled to RT, poured into a mixture of 5 g of ice and 5 mL of 25% ammonia solution, and then stirred for 2 hs. The precipitated product was filtered off, washed with water and dried to yield 350 mg of 5-methylindole-2-carboxamide. 1H NMR (600 MHz, DMSO-d6): δ 11.37 (s, 1H), 7.89 (br, 1H), 7.36 (s, 1H), 7.30 (d, 1H, J=8.4 Hz), 7.28 (br, 1H), 7.02 (s, 1H), 6.99, (d, 1H, J=8.4 Hz), 2.36 (s, 3H). 13C NMR (150 MHz, CDCl3): δC 160.95, 132.95, 129.77, 126.15, 125.44, 123.10, 118.77, 110.02, 100.65, 19.20.

後処理

  1. temperaturewas refluxed for 2 hs
  2. filtrationThe precipitated product was filtered off
  3. washwashed with water
  4. customdried

出典と根拠

ORDレコード
ord-71ea8f242a0b4aa5971da05f7db0ab19
出典データセット
uspto-grants-2015_12
特許番号
US09216993B2

関連ノート

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