Sodium Carbonate → HCID 9885864, compound

HRID 1595754Notes

Reaction equation

HRID 1595754 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[NH2:20][C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[N:26][NH:27]2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:15][CH2:16][CH3:17])[N:5]=[CH:4][C:3]([C:18]#[N:19])=[C:2]2[NH:20][C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[N:26][NH:27]2)=[CH:23][CH:22]=1)[CH3:14]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 814231H-Indazol-6-amineHCID 107788724-Chloro-6,7-diethoxyquinoline-3-carbonitrile

Product 1

HCID 9885864HCID 9885864, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 250 mg (1.88 mM) of 6-aminoindazole in 10 ml of ethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100° C., then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80° C. to yield 448 mg of 6,7-Diethoxy-4-(1H-indazol-6-ylamino)-quinoline-3-carbonitrile as a tan solid: mass spectrum (electrospray, m/e): M+H 374.1, mp=143-145° C.

Workup

  1. customThe solid was collected
  2. washwashed with water
  3. customdried under vacuum at 80° C.

Sources & evidence

ORD record
ord-82b77f7ad37841d99a258841f27e395d
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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