Potassium Carbonate → HCID 68001564, compound

HRID 1427415Notes

Reaction equation

HRID 1427415 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2.C([O-])([O-])=O.[K+].[K+].Cl[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH2:28])[C:23]=1[N+:29]([O-:31])=[O:30]>CS(C)=O.O>[NH2:28][C:24]1[C:23]([N+:29]([O-:31])=[O:30])=[C:22]([O:14][C:11]2[C:10]3[N:9]=[CH:8][CH:7]=[CH:6][C:5]=3[C:4]([NH2:3])=[CH:13][CH:12]=2)[CH:27]=[CH:26][N:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 40716944-Chloro-3-nitropyridin-2-amineHCID 162119475-Aminoquinolin-8-ol--hydrogen chloride (1/2)

Product 1

HCID 68001564HCID 68001564, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 5-aminoquinolin-8-ol dihydrochloride (2.00 g, 8.60 mmol) in DMSO (30 mL) under N2 was added K2CO3 (3.79 g, 27.5 mmol) and after 1 hr at RT the mixture was treated with 4-chloro-3-nitropyridin-2-amine (1.34 g, 7.72 mmol) in a single portion. The reaction mixture was heated to 70° C. for 2 hr and was then cooled to RT and diluted with water (500 mL). A precipitate formed which was isolated by filtration, washed with water (2×20 mL) and then dried in vacuo at 40° C. to afford the title compound, Intermediate H1 as a dark brown solid (1.50 g, 53%); Rt 0.99 min (Method 2); m/z 298 (M+H)+ (ES+).

Workup

  1. temperaturewas then cooled to RT
  2. customA precipitate formed which
  3. customwas isolated by filtration
  4. washwashed with water (2×20 mL)
  5. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-1b04485f1d9d42378dfdcd7ff58a55bb
Source dataset
uspto-grants-2015_01
Patent number
US08933228B2

Reaction notes

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