Ammonia → 9-[(Cyclohexyl)methyl]-4-hydroxy-5-carbamoyl carbazole

HRID 567366ノート

反応式

HRID 567366 の反応式
[CH:1]1([CH2:7][N:8]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][C:13]=3[C:22]([O:24]C)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:26]>C1COCC1.[OH-].[NH4+]>[CH:1]1([CH2:7][N:8]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][C:13]=3[C:22](=[O:24])[NH2:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 222AmmoniaHCID 227405539-[(Cyclohexyl)methyl]-4-hydroxy-5-carbomethoxy carbazole

生成物 1

HCID 227381839-[(Cyclohexyl)methyl]-4-hydroxy-5-carbamoyl carbazole収率 70%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 14923Ammonium Hydroxide溶媒

反応条件

温度
35 °C

実験手順

A solution of 9-[(cyclohexyl)methyl]-4-hydroxy-5-carbomethoxy carbazole (205 mg, 0.608 mmol) in 5 mL of THF and 20 mL of concentrated aqueous ammonium hydroxide was treated with a stream of NH3 gas to ensure saturation. The reaction vessel was capped, and the mixture was heated at 35° C. with stirring until tlc indicated complete consumption of starting material (20 hrs). The THF was evaporated, and the aqueous layer was filtered. The green solid precipitate was dissolved in THF and purified by radial chromatography on silica gel (elution with CH2Cl2). The resultant foam was triturated with ether to afford 138 mg (70%) of the title compound as an off-white solid. IR (KBr, cm−1) 3418, 3200, 3131, 1629, 1600, 1443, 1261, 778. 'FAB HRMS m/e, Calcd for C20H23N2O2: 323.1760. Found: 323.1760 (M+1).

後処理

  1. customThe reaction vessel was capped
  2. customconsumption of starting material (20 hrs)
  3. customThe THF was evaporated
  4. filtrationthe aqueous layer was filtered
  5. dissolutionThe green solid precipitate was dissolved in THF
  6. custompurified by radial chromatography on silica gel (elution with CH2Cl2)
  7. customThe resultant foam was triturated with ether

出典と根拠

ORDレコード
ord-b3b9d1ceb8c64eb9b8dc54be8bf6ab2d
出典データセット
uspto-grants-2001_01
特許番号
US06177440B1

反応ノート

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