Ammonium Acetate → 4-amino-8-(cyclopentyloxy)-7-methoxyquinolin-2(1H)-one

HRID 659057Notes

Reaction equation

HRID 659057 reaction equation
[CH:1]1([O:6][C:7]2[C:8]([O:19][CH3:20])=[CH:9][CH:10]=[C:11]3[C:16]=2[NH:15][C:14](=[O:17])[CH:13]=[C:12]3O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:25]>C1(C)C=CC=C(C)C=1>[NH2:25][C:12]1[C:11]2[C:16](=[C:7]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]([O:19][CH3:20])=[CH:9][CH:10]=2)[NH:15][C:14](=[O:17])[CH:13]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 667818648-(cyclopentyloxy)-4-hydroxy-7-methoxyquinolin-2(1H)-one

Product 1

HCID 667812934-amino-8-(cyclopentyloxy)-7-methoxyquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 8-(cyclopentyloxy)-4-hydroxy-7-methoxyquinolin-2(1H)-one (350 mg, 1.3 mmol), ammonium acetate (4.0 g, 52 mmol), and anhydrous m-xylene (10 mL) was heated at 150° C. under N2 for 48 h and then allowed to cool to rt. The mixture was concentrated to dryness, diluted with water (25 mL), stirred for 2 min, sonicated for 1 min, and then stirred for 5 min. The free-flowing solid was filtered, washed with water (25 mL), and pumped to dryness to give 4-amino-8-(cyclopentyloxy)-7-methoxyquinolin-2(1H)-one: MS (ESI): 274.9.

Workup

  1. temperatureto cool to rt
  2. concentrationThe mixture was concentrated to dryness
  3. additiondiluted with water (25 mL)
  4. customsonicated for 1 min
  5. stirringstirred for 5 min
  6. filtrationThe free-flowing solid was filtered
  7. washwashed with water (25 mL)

Sources & evidence

ORD record
ord-5017b71545b14f729736350a1aaf6d5e
Source dataset
uspto-grants-2011_12
Patent number
US08080563B2

Reaction notes

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