Water → Methyl 3-methyl-1H-indole-6-carboxylate

HRID 392215

反応式

HRID 392215 の反応式
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([BH3-])#N.[Na+].O>CN(C)C=O.S1(CCCC1)(=O)=O>[CH3:1][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1

参加物

7

反応物 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 735867methyl 3-formyl-1H-indole-6-carboxylateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 21938240Methyl 3-methyl-1H-indole-6-carboxylate収率 91.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 31347Sulfolane溶媒

反応条件

温度
100 °C

実験手順

A mixture of methyl 3-formyl-1H-indole-6-carboxylate (12.0 g), p-toluenesulphonic acid (2.0 g) and p-toluenesulphonylhydrazide (13.0 g) in a mixture of dimethylformamide (100 ml) and sulpholane (50 ml) was heated at 100° C. for 15 minutes and then cooled to room temperature. The mixture was treated with sodium cyanoborohydride (15.0 g, 5 g portions after 10 minute intervals), then heated at 100° C. for 2 hours. After cooling to ambient temperature the reaction mixture was treated with ice water (500 ml) giving a white precipitate. Water (1000 ml) was added and the mixture stirred for 30 minutes then filtered. The off-white solid was washed with warm water then azeotroped with toluene to yield the title compound (10.2 g) as a white solid.

後処理

  1. temperaturecooled to room temperature
  2. temperatureheated at 100° C. for 2 hours
  3. temperatureAfter cooling to ambient temperature the reaction mixture
  4. customgiving a white precipitate
  5. filtrationthen filtered
  6. washThe off-white solid was washed with warm water
  7. customthen azeotroped with toluene

出典と根拠

ORDレコード
ord-bfce7c81643c40b4a05d1623efd7841b
出典データセット
uspto-grants-2004_10
特許番号
US06800645B1

関連ノート

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