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

HRID 51458ノート

反応式

HRID 51458 の反応式
[CH:1]1([CH2:6][N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:20])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][C:12]=3[C:21]([O:23]C)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:25]>C1COCC1.[OH-].[NH4+]>[CH:1]1([CH2:6][N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:20])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][C:12]=3[C:21](=[O:23])[NH2:25])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 222AmmoniaHCID 227382539-[(Cyclopentyl)methyl]-4-hydroxy-5-carbomethoxy carbazole

生成物 1

HCID 227382079-[(Cyclopentyl)methyl]-4-hydroxy-5-carbamoyl carbazole

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-[(cyclopentyl)methyl]-4-hydroxy-5-carbomethoxy carbazole (110 mg, 0.34 mmol) in 3 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 heated to 35° C. with stirring until tlc indicated complete consumption of starting material (20 h). The THF was evaporated, and the aqueous layer was filtered. The resultant solid was triturated with ether to afford 50 mg (0.162; 48%) of the title compound as a greenish-white solid. IR (KBr, cm−1) 3416, 3199, 3126, 1630, 1599. 1442, 1262, 778. 'FAB HRMS m/e, Calcd for C20H21N2O2: 309.1603. Found: 309.1607 (M+1).

後処理

  1. customThe reaction vessel was capped
  2. customconsumption of starting material (20 h)
  3. customThe THF was evaporated
  4. filtrationthe aqueous layer was filtered
  5. customThe resultant solid was triturated with ether

出典と根拠

ORDレコード
ord-0ed2252eb6d5453087a00cbd681d3793
出典データセット
uspto-grants-2004_03
特許番号
US06713645B1

反応ノート

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