Hydrochloric Acid → HCID 67201128, compound

HRID 547534Notes

Reaction equation

HRID 547534 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH2:6][C:5]2=[O:12].[CH2:13]=O.[BH3-][C:16]#[N:17].[Na+].Cl>CCO>[CH3:13][N:17]([CH3:16])[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH2:6][C:5]2=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67198430HCID 67198430, compound

Product 1

HCID 67201128HCID 67201128, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-amino-4-quinolone (01) (112 mg, 0.71 mmol) and aqueous formaldehyde (40% w/v, 1.6 mL, 21.2 mmol) in EtOH (10 mL) were sequentially added NaBH3CN (335 mg, 5.67 mmol) and 1N HCl (2.8 mL, 2.8 mmol), and the resulting bright yellow suspension was stirred at room temperature for 15 minutes. After this time, solvent was removed under reduced pressure, and the residue then dried by two MeOH azeotrope cycles. The residue was resuspended in MeOH and filtered through Celite, and solvent was removed under reduced pressure. The residue was crystallized from MeOH:EtOAc to give 6-dimethylamino-4-quinolone (O2) (80 mg, 60%) as an amorphous tan solid; 1H NMR [(CD3)2SO] δ2.93 [s, 6H, ArN(CH3)2], 5.90 [d, J=7.00 Hz, 1H, ArH], 7.13 [br s, ArOH], 7.24 [m, 2H, ArH], 7.45 [dd, J=7.41, 2.29 Hz, 1H, ArH], 7.74 [d, J=7.00 Hz, 1H, ArH]. LCMS (APCI+): 189 (100%). Rf=0.48 (10% MeOH:CH2Cl2).

Workup

  1. customAfter this time, solvent was removed under reduced pressure
  2. dry with materialthe residue then dried by two MeOH azeotrope cycles
  3. filtrationfiltered through Celite, and solvent
  4. customwas removed under reduced pressure
  5. customThe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-32ad6688a53a4c9ca62b8ece9a85a10e
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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