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

HRID 51453Notes

Reaction equation

[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

Participants

Conditions

Temperature: 35 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-f5d528bab89d4d118d3d4fdc70b1fc6d
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713645B1

Reaction notes

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