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

HRID 567371Notes

Reaction equation

HRID 567371 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-dbf94fbd631e4b1598fbdab7cd4e3d4b
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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