Sodium Carbonate → HCID 21704775, compound

HRID 1595779Notes

Reaction equation

HRID 1595779 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[CH3:18][C:19]1[C:25]2[CH:26]=[CH:27][C:28]([NH2:30])=[CH:29][C:24]=2[NH:23][C:21](=[O:22])[CH:20]=1.Cl.N1C=CC=CC=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][C:3]([C:16]#[N:17])=[C:2]2[NH:30][C:28]1[CH:29]=[C:24]2[C:25]([C:19]([CH3:18])=[CH:20][C:21](=[O:22])[NH:23]2)=[CH:26][CH:27]=1

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 882777-Amino-4-methyl-2-quinolinoneHCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 21704775HCID 21704775, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.174 g of carbostyril 124, 0.020 g of pyridine hydrochloride, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. The mixture was cooled and added to 40 ml of water. To this mixture was added sodium carbonate to pH 9. The product was collected, washed with water, and dried to give 0.356 g of 6,7-dimethoxy-4-(4-methyl-2-oxo-1,2-dihydro-quinolin-7-ylamino)-quinoline-3-carbonitrile as a solid, mp>300° C.; mass spectrum (electrospray, m/e): M+H 387.1446.

Workup

  1. temperatureat reflux temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2ec16a7679c64672b8fac12e7339b6f2
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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