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

HRID 51458Notes

Reaction equation

HRID 51458 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
35 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0ed2252eb6d5453087a00cbd681d3793
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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